You’ve heard us say before that this is the best time in history for women to be single – and everyone else on the planet, too.

I know you’re skeptical. If you’re frustrated in dating and feeling like you don’t have good dating options then this show is for you.

Today, I have a very special co-host joining Damona. You may remember him as her co-host from the groundbreaking TV series #BlackLove where they teamed up to teach black women how to date in New York City. Hard to believe but this year will mark 5 years since that groundbreaking show was made. 

Jack Daniels – aka the King of Breakthroughs – is a psychotherapist and founder of the Good Men Introduction Agency, a new twist on dating. 

He is a 5-time bestselling author of books like “Stay Out of Your Own Way” and “I Need a Wife – Where are the Real Women?”

You’ve seen Jack in Fox News, Bravo, A&E, Nightline, Lifetime, CBS, NBC, NPR, Real Housewives of Atlanta, and so much more!

And now he’s here to answer the question: where are all the good men?

More on that later, first we have headlines!



Are there actually plenty of fish in the sea?

According to this article from the Atlantic, dating economists argue that dating is not a 1:1 market. What does this mean for you? Damona and Jack break it down.

Finally a reality show for single seniors!

The Hollywood Reporter tells us that ABC has announced a “Bachelor for seniors.” Damona thinks this is a great concept for a forgotten market. Does Jack agree? 


Should you date in the workplace?

Recently, WeWork announced that a member of their executive staff has stepped down after promoting someone he was in a relationship with. Damona is very adamant that you should not date in the workplace (Bonus Reading: Damona’s NPR LifeKit episode on dating in the workplace.) Jack disagrees!




Jack tells us about his new approach to dating! If you are feeling stuck in your city, trying to find all the good matches, his dating introduction service might just be the solution for you.



Find Jack at jackadaniels.tv and join the list at goodmen.tv!




Submit your questions Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

  • EMAIL from D – I’m a soon to be 40/male and I’ve never had a girlfriend or hooked up with anyone. It’s not that I think I am unattractive physically, I just feel like I’d be viewed as something sub-human if I revealed my lack of dating skills – I basically never get past a first date and  I wonder if there’s any hope. 
  • DM from Lisa – Curious after how many dates you should have the “are we exclusive talk”



Damona  0:12  

Hello Lovers, Happy Women’s History Month. So you’ve heard me say before, that I believe this is the best time in history for women to be single. And actually for everyone else on the planet to be single and dating too. I know you’re skeptical, right? If you’re frustrated in dating and you feel like you don’t have good dating options available, then this show today is for you. Today I have a very special guest joining me You may remember him as my co host from the TV series hashtag black love. We teamed up then to teach black women how to date in New York City for that show and it’s hard to believe that this year will mark five years since that groundbreaking show is made. jack daniels is the king of breakthroughs. He’s a psycho therapist and founder of the good men introduction agency, which is a new twist on dating and matchmaking. He’s the five time best selling author of books like stay out of your own way. And I need a wife. Where are the real women? You’ve seen jack on Fox News, Bravo, Annie nightline lifetime and so much more and now reunited and it feels so good. Please help me give big smooches to jack daniels.

Jack A Daniels  1:39  

What’s happenin! I’m excited to be here. I’m excited for you. Almost like 300 episodes in oh my goodness, you are killing it right now.

Damona  1:55  

Well, it’s amazing to have you here and it’s amazing to hear your take on the topics will be dishing about today, including our they’re actually plenty efficiency, dating economists say no. And finally, a new reality show for single seniors. Plus, should you date someone at work will tell you the pros and cons and then we’ll answer your questions including, is there no hope if you just can’t get past the first date? And how many dates should you go on until you have the DTR? Talk? All that and more on today’s dates and mates? jack? Are you ready to hit these headlines?

Jack A Daniels  2:33  

Oh, no, those are those are some deep topics we don’t have. Well, we’re in it. Now. I got some stuff to say. These dating dish.

Damona  2:43  

According to the Atlantic, there was a according to the Atlantic, we have to look at dating in a whole different way. There was a very in depth article about the economics of dating and they acknowledge that most people Think of dating as a numbers game, but they were saying that that approach actually can make you suppress your honest expression of how you’re really feeling about dating. It can drive you into loneliness. And it can force you to keep this this desire to find a relationship but but feel like you’re not getting your needs met online and yet you keep doing it because you can’t stop because you’re addicted to it. JACK. I know we’ve been we’ve been doing this for a long time together. But I want to know what you think about dating today. Do you see it as a numbers game?

Jack A Daniels  3:40  

I see it as a mess.

Jack A Daniels  3:45  

Can you be more specific, sir?

Jack A Daniels  3:48  

When you say like a numbers game, I see. So I’ve done this. I’ve done this for a while. And the hardest thing for people to do is to pick right and the more option You have the harder is going to be to actually pick. So they did this interesting study and I can’t remember what university it was at, but it was they did a they did a study in a grocery store, and they were trying to see in survey who bought jelly. So they put out like 16 bottles of jelly in different flavors, different packaging, and then it had people taste them. And they were trying to discern who was actually going to buy the jelly. So they put out 16 and then they put out for statistically 30 was it 30% more people bought when it was only four bottles of jelly versus 16. Meaning that when there’s more options that are available, you can’t make a decision. And it’s just like that when you’re talking about dating, it’s just like that in this dating. There are too many options available. I mean, if I don’t like this one, I can go to this one. If I want Like I can swipe left, swipe right, all these different swipe, swipe, swipe? Is there too many options? I used to be like, you know, I dated the girl from neighborhood or from from high school, right? But today, it’s like, if there’s an infinite number of possibilities that are available, and I think people were taking advantage of it.

Damona  5:21  

Okay, we have to break that down. Because obviously, I’m a big believer in online dating. And we have seen a big shift, like you were saying, since even just the 1950s, where your dating pool was basically just the five people who were your age in your town, and as people moved into cities and started to form their own social circles, and we could get into a whole conversation about the way that birth control affected people’s ability to have relationships out, necessarily having to marry that person. There’s so many layers to this conversation. But I think what there is a problem right now in, in dating apps, because we’re shopping, we’re buying the jelly but we don’t we never read the label. We don’t know what’s in it, right? We don’t we don’t know how many calories it has. We don’t know if it’s using GMOs. And we’re just like, oh, that jelly looks good. And we just pick it off the shelf. And then all of a sudden, we’re like, I just read one. Right. And before, like, when I met my husband online, the the application process, the profile creation was very, very thorough. So I felt like I was dating better than because I actually knew more about that person than if I met them by chance. But now we’ve almost done a 180. And now we’re meeting people by chance, except for we’re meeting them on a dating app. And they’re just don’t really know anything and like you said, it is a swipe, swipe. So we’re not making a connection to the people and it’s it’s like this article Saying people are looking at dating someone. It’s like a commodity, but it’s a commodity with feelings. It’s not grape jelly.

Jack A Daniels  7:09  

What’s crazy Shelly, right? What’s interesting to me is the whole connection piece. And I think that it’s become so static, that we don’t even look at people as people anymore. Because it I mean, and I’m not saying this to put down like online dating, but I’m saying if I’m looking at a static picture, I’m looking at a picture versus a person. And I don’t have a chance to get to know that person because my insecurities or the things that I value or I don’t value or that I’m heard about the last in the last relationship or from the last relationship, they show up in a way that doesn’t allow me to actually like or get to know this person. And I don’t I don’t get smeller hair hugger. I don’t want to know if she has like, like stinky perfume or, you know, like all of those things that attract us are repelling us a little bit because everything static right now and I don’t have a chance to actually connect, you

Damona  8:13  

brought up a really important point that leads us to our next headline about when you are older. Sometimes it feels like you don’t have as many dating options. And as a response to this The Bachelor for the first time they put out a casting call looking for singles over 65 they’re saying, Are you are you entering your golden years and looking for romance? If so, you could be on the bachelor and I hear this all the time. As someone that also does a lot of TV. A lot of times, I’ll ask my people on my mailing list like would you want to be on a show and many times the TV networks are saying they just want it for what quote their audience. So they want someone 25 to 35 and I will I’ve just I’m just putting out the call I’ll get a lot of angry emails towards me of like, Well, what about me? I’m over 65 I’m still looking for love. Why isn’t there a show for me? Now they have answered your prayers. JACK, what do you think this, this show will be like? And do you think people are actually going to want to watch someone over 65 fine, left?

Jack A Daniels  9:19  


Jack A Daniels  9:22  

There’s not an eat. There’s not a day that goes by I don’t get an email from someone over the age of 55 and saying, I want love to. I think it’s a fantastic idea and a forgotten market that hasn’t been tapped into it because you got a lot. You got a lot of spunky, you know, 60 plus year olds that are really like, I mean, I had a guy just I just had a speaking engagement like a couple days ago. guy was like, Hey, I’m out here. He’s like, he’s like 60 bucks. But here’s the thing that I found and I don’t know if you if you found this damona But what I found about People and somebody needs to do something. But what I found and discovered in my experiences is that and the reason I don’t offer the service for elder people, I haven’t been able to find quality connections for women that are of that age, because the men are not checking for the women

Jack A Daniels  10:24  

at a parallel age,

Damona  10:25  

but I feel like I feel like that is a what they what you put on a an application or what you say you want, and who you’re attracted to are two different things. And so what I try to do with women over 65 is make sure that they don’t go into it with the mindset of everyone. My age only wants to date someone younger because then then you’re then you might as well just stay at home and what


Jack A Daniels  10:51  

I’m just I’m like every guy I’ve met,


Damona  10:56  

because they’re reporting it, but that doesn’t mean that if they’re attracted to a woman A man who is 65, who’s their own age, they won’t go out with her. And that’s what studies studies show. Men will if you want, because if they find you attractive, they will still go out with you.

Jack A Daniels  11:09  

It’s true.

Jack A Daniels  11:12  

I don’t know, jack, we gotta give the latest

Jack A Daniels  11:15  

interesting to watch, because I think a lot of what we’re talking about is actually going to come up on the show. I know it’s gonna come a horror show. I think it’s just going to be one of those things that I would love to see how to do it just so I could tell my mom how to do it a little bit better in the streets, send your mom

Damona  11:35  

on the line and we’re gonna hook her up and you’ll see what I’m talking about. This is why I love I love talking with you jack because we have different perspectives, but we we both want the same thing we want people to find love, but I gotta tell you one place that I do not recommend looking for love is at work. I just did an NPR podcast called Life kit where I shot down all the reasons Why you should not you should not i, where i talked about all the reasons why you should not date someone at work. And here we have another another major scandal we work executive stuffed down this week due to a relationship. His name is Grant McGrail. He was VP of account sales, and he’s now under investigation for a romantic relationship with a team member whom he promoted. And what I said on the life kit episode is that it’s not just about you, when you’re dating in the workplace, you have to consider what are the consequences for other people and here, you know, somebody didn’t get that promotion they were looking for and they’re like, Well, except for Grant has been banging this other chick and not telling the company about it. So I have a hard line on dating at work, jack, but, you know, I that’s just my perspective. What do you think?

Jack A Daniels  12:55  

As a tough one for me because I actually date the person I work with so no,

Damona  12:58  

but you weren’t dating before. You nowadays? Well, now you’re married to someone that you work with, but you built that together.

Jack A Daniels  13:06  

Yeah, you know, I used to be a manager in corporate America. And it’s, that’s a tough question because we spend 70 80% of our lives at work, and the other 20% of going home, and I’m by myself. So if I’m surrounded by people that are of the same age, we have the same compatibilities, the same likeness, and we’re both single. I’m kinda like, this shouldn’t be anything wrong with it, if we’re both equals Now, if the story that you just told he was her superior and she was his subordinate, it gets a little, just a little fun tracking. At the same time, I’m almost like, I’ve dealt so much with human resource issues if they are two consenting adults dolt, and no one is heavily benefiting from the relationship. And they’re just consensual adults having a relationship I don’t really see that much wrong with and I know there’s some complications that can occur. I know that there’s some some. It’s just it’s a touchy subject. So I don’t want to like put my foot in my mouth as a guy. Because I don’t I don’t want to be that guy. But I would. I’ll say this, I would never do it. Only because I know that it’s a tough situation. But I have been around people that have found love and work. And it’s not like, Yeah, he was her boss, or she was his boss. And they couldn’t reveal their relationship at work because of whatever the Code of Conduct was, but they were in love. So I’m like, you know, you got two people that love each other, like, let them do what they do.

Damona  15:01  

Well, I respect that opinion. And no, no, no, I respect that opinion. And I know sometimes you don’t you can’t control who you fall for. I would just say think through it. Think of the possible consequences. You can listen to my life get episode, I’ll put a link in the show notes, and see all that like, go through the checklist and really think about it. Because this is another thing, and we’ll talk about this a little bit more after the break. Do you have to go into love mindfully today, and I feel like one reason that so many people are frustrated is that we’re kind of dating by chance out here and we’re swiping right and left like you were saying, and we’re like, oh, I spend 80% of my time at work. So I’m just going to date someone here. And there isn’t enough consciousness around who you’re choosing to, to be with and I know this is something that you’ve you’ve dedicated several books and a lot of your your own personal, personal life, to finding someone That’s not just a match, but someone who’s the right match. So after the break, I want to hear more about your own love story. And what the kind of transformations that you’ve created for people in the all the many years that you’ve been doing this, so stick around with me jack Well, yeah,

Jack A Daniels  16:16  

I’m not going anyways,

Jack A Daniels  16:19  

we’ll be right. We’ll be right back.

Damona  16:28  

We are back here with jack daniels, my co host from the TV show hashtag black love. And jack you know your You are so great at giving advice and helping people see what they really need in love and creating a path to get there. Thank you. But I know you’ve been there before on the path that many of our listeners are on and it hasn’t always been smooth. Can you tell us a little bit about your own love story and then where you’re from Relationship statuses today

Jack A Daniels  17:01  

was actually married before to my college sweetheart. We were in love. Everyone looked up to us. And we were like that it couple and we were young. But we were going through life together and everything was great. Everything was fine. Until one day she came home and she said, I don’t want to be married anymore. I was in shambles. And I was totally out of my element. And I’m sitting there in this house with half the furniture gone because she taken it. I’m sitting in I hear this voice that tells me like, stay out of your own way. The phrase, I’d never heard it before. I’ve never seen it and I’ve read it before this was years ago. And that phrase literally changed the trajectory of my life. It it changed who I was inside. I mean I shaved. I cut my hair. I got myself back together, I picked myself off of that Florida I was curled up in a fetal position and I went, and I started activating and walking more in purpose. I quit the job that I hated. And I did all of that. But that’s not even the best part of what it was that I stepped into after I got up off of that floor after I wrote that phrase and sealed it in and embraced staying out of my own way. The best part is I married my best friend five years ago is such a blessing because it has allowed me to just just have and find the love of my life, but also be the love of my life because now I love myself better and because I love myself better. I’m able to love a lot more people not just my wife and my three future girls, I’m about to be a girl dad joined so yes, yes, it just I’m full of love and I love for other people to have it in Well, so,

Damona  19:01  

so I want to talk about before you, I, I’m so happy for you, jack and I, when we first met five years ago, you guys were newlyweds. And I was like, oh, and you were just building the life. So it’s really beautiful to see it come full circle for you. But before, there’s a part of the story that I know our listeners are like, But wait, in addition to filling yourself up and feel it being on purpose, and getting out of your own way. There were other actions that you did take to bring the right woman into your circle. And I know you wrote a book and you did also a tour on the topic. It was called the book is called I need a wife. We’re are the real women. And I know for a lot of our listeners, they’re like, I totally relate to that. Where are the real women? were the real men. Can you tell us a little bit about what that tour was? And do you feel like it did bring the real woman into your life that you should be.

Jack A Daniels  20:02  

Yeah, yeah. It’s funny you remember that? That’s good. Um,

Jack A Daniels  20:07  

the key word is intention. intention is so big for me. I’m intentional about everything that I do. And I don’t do it just to be doing, you know, going through the motions. And I think that most people just walk through life blindfolded. Just jaywalking. Like, like I, but I’m extremely intentional. So I need a wife, where the real women that was my fifth book, huge. And what we did was we did this tour, we toured 14 different cities, over 22,000 people showed up and we had all of these guys on these panels that are saying, Hey, I’m single, successful and ready to be married, but I can’t seem to find a quality woman. I’m like, I okay, I’ll put you out there player. So, we went to all these different cities and we had all these different guests. That are saying, Hey, I love it. And they were talking about relationships, and sex and commitment and all these different things. And for me, I used to walk around with a shirt that said, I need a wife right there was I wasn’t looking

Jack A Daniels  21:16  

vulnerable though to even say

Jack A Daniels  21:20  

I don’t think I was in my head. I wasn’t doing it for me, but subconsciously, I wanted that I still want even though I was hurt, even though by most men standards, I’d be damaged goods, because I can go and I can go because if that happened if movement most men get hurt like that, they go and they try to hold a way out of healing.

Jack A Daniels  21:43  

Right? They go their way out of here.

Jack A Daniels  21:46  

Oh, yeah, they just like they go smash everything in like, Okay, well, I don’t trust women. I don’t want it happens. Council like, it happens.

Jack A Daniels  21:56  

It happens with women too, by the way,

Jack A Daniels  21:58  

I know and i’ll get I was one saying I calcium, so many people. So I hear the real truth about what’s going to let you sleep away.

Damona  22:08  

But I said, Yeah, but it’s empty. It’s not you’re chasing a connection.

Jack A Daniels  22:12  

It’s just it’s you, you’re looking for something. So for me, the connection that I was searching for was, hopefully I can give that to someone else. Like if I can help someone else receive this. Maybe I’d be blessed enough to see with myself. That was a lie. I wasn’t given just to get but I was thinking like, well, maybe this is my purpose, my calling. So what I want people to understand is that it’s not just about activating your calling and your purpose, but it’s being intentional about what your love story is going to be creating a love story that makes sense to you and playing a pivotal role in that love story. instead of allowing somebody else to direct it. Like you, you are the director. So if you want something You need to go after another thing that I want to say. And I think this is really important because I didn’t do this on my own. Yes, I was able to get clarity about what it was that I wanted, but I was also able to get help. And sometimes people think that they can do it all by themselves, it’s okay to raise your hand and say, I need a little bit of help. So I went got counseling, too, because I had some stuff had some stuff that I needed to clear out. And to your point, damona I could have utilized that stuff as a starting point to be able to just become the most outrageous hole in the world. But I wanted to I wanted to deal with what it was that I was feeling and that’s

Damona  23:49  

so I don’t we all have stuff like I’m sure there are a lot of people listening that are like, Oh, I’m operating from my stuff instead of

Jack A Daniels  23:59  

have to acknowledge You deal with it is you can’t fix what you can’t face. And I needed to face what it was and who it was that I was about to become. Because I didn’t want to be that person. So we were at a country and we had all of these guys that were saying, Hey, man, I love I love women. And we hooked up so many men 73% of all of the guys that were on that tour, and I’m talking about the people that I picked to be on stages with me. 73% of all of them are now either engaged or married. Wow. And like all

Jack A Daniels  24:37  

good stats. Yeah.

Jack A Daniels  24:39  

We mixed and mingled and we brought all these people together and women were saying, what, where are the good men? Here they are right here. They right here.

Damona  24:47  

So now you’re you’re extending this, you’re you’re still creating connections and opportunities for people who are relationship minded to get out there. So tell us a little bit more about this next phase. Is of evolution for you.

Jack A Daniels  25:01  

So I was still traveling around and I was still, like, intermittently, I wasn’t doing a lot. But everywhere I went, I was doing speaking and storytelling seminars and teach people how to tell their stories and clarify their messages, etc, etc. And people were still asking like, well, where all the good men, like? You keep saying this whole bunch of good man. What again? What am I supposed to do that started this campaign that would tell women like, you know, he can’t find you on the couch.

Jack A Daniels  25:35  

That’s right. That’s right. Like

Jack A Daniels  25:36  

for the last three and a half years, I’ve been saying the same and he can’t find you on your couch. You got to get off the couch, to be able to do something and I know it’s like the online thing and, you know, online dating, etc, etc. So,

Damona  25:51  

I do not but I just have to say as far as online dating, I have to remind everyone that if you’re not actually going on dates, you are not dating There you have a profile that did. Yes. So I’m with you, you got to do something.

Jack A Daniels  26:07  

Yeah. So are visible.

Jack A Daniels  26:09  

So I was I was encouraged or encouraging people to get off the couch and to get offline. And I was encouraging people to do it. But I didn’t have a solution or a strategy or a mechanism for them to actually do it. Because the next question that they were asking me, well, well, where should I go jack? And I’m like, Hmm, that’s a good question. I can answer it. I could tell you or I can show you. So what we did was we said, okay, got all these women. In First of all, there are several great guys out here. I just think that I’m going to say this. I’m just gonna mess up some people I’m just gonna like mess with I’m gonna mess with your listeners just a little bit. I don’t think that there’s a dating problem. Don’t think that there’s like a huge male shortage. I just think women are stingy. What? Wait a minute, let us sink in. Let us say stingy, what do you mean by that? I think women are stingy. And here’s what I mean by that before y’all start throwing tomatoes at your phone. Women have the capacity to be able to fix the shortage tomorrow. Here’s how every woman I talked to has a cell phone, take out your cell phone right now you look at it, scroll through the contacts list. Let’s go to that do not answer list. Let’s go to that list of all the guys that you’ve either dated, don’t want for yourself or don’t like, all of those guys are potential matches for someone else. Just give me five of those guys that you dated, don’t or didn’t want for yourself. They don’t have to be right for you. They’re great for someone else. Let me go through your cell phone. Pick out those guys. I’m gonna take those guys. swap them. With your gut, like put them, put them with somebody else that’s actually compatible with that type of guy, and then take whatever 50 that I come back with because I talked to 10 different women, and I got a pool of like 50 guys, and I’m just going to match you and give you an opportunity to be able to say, Okay, well, I didn’t really have any options at first because all these people I like, but now I have like 45 options available in front of me. Women can fix the problem if they weren’t so mg.

Jack A Daniels  28:35  

So they’re keeping me it’s funny like my husband and I had a conversation about this.

Damona  28:40  

After watching Little Women of all things, I was like, I don’t like Amy cuz girl code because Joe was with I forget the guy’s name at producer Leah. Leo knows who he was. Lori Thank you. Okay, so Joe. Joe was Like with Laura, like, they were like, they were hanging out like nothing was really happening. But he was in love with her. She was really in love with him, but she didn’t really want to acknowledge she wasn’t really in that place. And then her sister went and snatch this guy, and was like, Okay, well, I want to marry you. And then Joe was like, What happened? And I said, I said, Amy is not following girl code, and my husband could not understand. He was like, they did work. She didn’t want him Joe did.

Jack A Daniels  29:28  

What’s the big deal? So you’re

Jack A Daniels  29:30  

saying, My philosophy is dingy.

Jack A Daniels  29:35  

That’s the problem. That’s why women are singing, but his his thing and all see any

Jack A Daniels  29:39  

more Amy’s unless Joe says we’re so good, all seriousness,

Jack A Daniels  29:43  

I took that exact same philosophy that I’m talking about in terms of women being stingy. And I turned it into a business introduction service full of guys that are because I’ve been collecting men over the past few years and I’ve got this huge database of good quality men. got these great quality men and saying, Hey, I’m single successful, ready to be married, but can’t find a quality woman. And they’re looking. So I took that philosophy of saying, hey, women are stingy, but I got lots of guys and I created a club. It’s a club that basically the only way a woman can come into the club is that she has to invite two good men that she’s either dated dumped or didn’t want for so no excuses. I don’t want to hear I don’t know any. I don’t want to hear that. I don’t there aren’t any out there. Yes, there are tons of you got Facebook friends you got you go to church, you go to work. You go

Jack A Daniels  30:38  

castaways on dating

Jack A Daniels  30:41  

everybody you you have met we the way it just keeps funneling in multiple men. And then we take you and we pair you with your preferences, your likes, your your warts, and all the things that you’re looking for with guys that are compatible to you and we send you out own group dinner dates across the city in groups of six, or in groups of eight. So you got three guys, or in three girls or four guys, four girls, and it’s been working phenomenally.

Damona  31:13  

Okay, how can pick me I’m sold jack, I’m sold. How do people get in this database? How do they How do they bring their cast away guys and not be stingy because I know there’s a lot of ladies now that are like, I’m not stingy. I will show you jack daniels.

Jack A Daniels  31:28  

The first thing you gotta do is you can’t be stingy.

Jack A Daniels  31:31  

How can people get get invited to some of these events,

Jack A Daniels  31:35  

you can go to good men.tv at 10 million men.tv. And be put you basically be put on the waiting list because it got it was so good. We launched in six different cities across the country, and the numbers just went through the roof. I mean, we only were at I don’t wanna say echo back, we were overcapacity because people were looking for something different to You know, people are working, they’ve got kids, they don’t know where to go, they don’t have a strategy. They just want something set up for them in a way that they can basically just say, okay, as long as I know that I’m going here, the worst thing that can happen is that you come out with seven new friends. Like maybe maybe you don’t meet anybody that you’re compatible with, you know, but you got four chances to meet someone because you got four guys sitting across the table from you.

Jack A Daniels  32:26  

Like, like, you got some practice, you gotta practice a day

Jack A Daniels  32:30  

is actually your comfort zone. It takes you out of like, who you who you are, and and most importantly, it gets you off the couch. How about that? There we go.

Damona  32:40  

Yeah, to start somewhere. That is awesome. We will put the link in the show notes. But that’s not all jack. We have questions from our listeners In our next segment. So I hope you can stick around to answer those questions.

Jack A Daniels  32:52  

You have scared me away yet.

Damona  32:54  

Okay. Let’s keep going. All right. We will continue the conversation in just a moment when jack and I will be answering your questions in our final segment. But first, let me tell you about a new favorite podcast of mine. The only one in the room. How many of you felt like the only one in the room, the only one who’s still single the only one who wants a real relationship. This podcast talks about what it’s like to feel alone or others. It’s hosted by my friend Laura Cathcart Robbins, and the only one in the room tells raw and vulnerable accounts from people who are, like most of us, just eager to connect. The idea for the podcast originated in 2018 when Laura attended a writer’s retreat with some very big name people. And soon after her arrival, she realized that out of 600 attendees, she was the only black person in the room. When she got back home. She wrote about the experience that she had in the Huffington Post, and the article went viral. But then something even more surprising. happened. The morning after her piece went live, Laura woke up to find 568 direct messages in her inbox. She thought that the messages would all be from black people having a similar story, but they were from people of all walks of life, all ages, races, religions, and they all wrote her because they connected with her essay and identified with that feeling of being others. And it wasn’t long before Laura knew what she had to do. She wanted to create a platform for all of those stories to be shared and heard. And so her podcast was born. She said intimate interviews with Mario van Peebles, Jon Cryer, Rebecca Gayheart, Cynthia Bailey and so many others who bravely share their experience of being the only one in the room and how they thrived in spite of it. If you can relate to this feeling than the only one in the room podcast is for you. You can find it wherever you’re listening to the show right now or look for the link in the show notes. Okay, now it’s time for your favorite segment where we answer the questions that you’ve submitted to us through Instagram, Facebook, Twitter, and email. And now it’s time for technically dating. All right, jack, this person, this guy emailed me because he was inspired by a previous question on the show. That was from a 30 year old woman who was still a virgin was asking about dating. And I just mentioned this to say that if anyone is listening and has a question, and they’re like, Oh, this is just me, I’m the only one going through this, nobody else would care. I just want to you know, people care. Other people are helped by the advice that you request on this show. So this person has been inspired. I will call him D because he wanted to remain anonymous, but he emailed me and he said, I’m a soon to be 40 year old male, and I’ve never had a girlfriend or hooked up with anyone. It’s not that I think I’m attractive physically. I just feel like I’d be viewed as something subhuman if I revealed my lack of dating skills. I basically never get past the first date. And I wonder if there’s any hope. JACK, I need a male perspective on this. So and, and he clarified for me like by I’ve never hooked up with anyone’s like he hasn’t he, he hasn’t had sex with anyone.

Jack A Daniels  36:23  

And so he’s felt like will like 40 year old virgin,

Damona  36:27  

the real life 40 year old virgin. And when he has told women in the past that he’s dated that he is a virgin. He feels like they run away. They go on one day and an hour, but he said a lot of times they asked him about his sexual experience early on, and so he’s kind of caught in this space where he doesn’t know how to answer the question. But he also doesn’t know how to get past it and move into, you know, he wants he wants something. He’s a good man. He wants a good woman. What do you say jack?

Jack A Daniels  37:00  

This isn’t this isn’t this isn’t hard. Like, I think that oftentimes we paint ourselves into a corner. And the way that we think we should appear and some of the things that we think that we should be doing, we typically do it in a way that doesn’t allow us to actually attract the person that we should be attracting. So in let me let me make sense out of that a little bit more like a an example. If you have someone who says that, oh, okay, so I’m single, I’m a virgin. And I really want a woman. Like, okay, you just announced yourself as being single beta version. One a woman, instead of telling a better story that says, You know, I want a woman who respects my values, who is into me because of who I am and not what I can give her. And oftentimes, I run across Women who are more interested in what it is that they’re accustomed to, and that they’re used to, and the package that they are accustomed to having, which is why typically they probably single anyway. Instead of being open to the possibility of something different, I am someone that is different. I am someone who is probably not going to be the guy that you’re used to the guy that you have dated in your past, but I can be the last guy that you kiss. If you give me a chance.

Jack A Daniels  38:36  

You’re so smooth,

Jack A Daniels  38:37  

is it? No, but I’m saying

Jack A Daniels  38:40  

there’s a different story that he has to tell himself. D if you tell yourself this confidence is everything. I could say, I’ve never had sex before. Or I could say, you know, I just I’ve been waiting all my life, to meet the right woman to be able to give myself to I don’t know if that’s you But I’m hoping that we get a chance to know each other a little bit better that I can share that with someone like you.

Damona  39:08  

Right? He needs to approach it as it’s an asset. Because then then she’s gonna be like, Oh, I like now I could be right. Instead of a deficit instead of something that’s like your Scarlet Letter of whatever the Scarlet v. Looking at is a super it’s a superpower, you event so selective. You have been so mindful about your choices, that that you you are waiting for the right person. I, I don’t I do wonder though, there. I think there are a lot of questions in dating, that we ask that we don’t actually want to know the answer to. And I’m, I’m curious about all of the women that have asked him about a sexual history, because I feel like that’s one of those questions where it you know, it’s like those small talk questions like what, how does Your job how’s your day? Like, you know, I don’t know, do I really do a really care? How’s your job? Or am I just asking it? Because I don’t know what else to ask? Yeah, yeah. So how can you answer that question if he’s asked again?

Jack A Daniels  40:18  

Okay, so there’s a couple of a couple different things. One, he said he’s not making it past the first date. Why are you talking about this on the first date number one, like you shouldn’t be talking about anything physical on the first date, period, you should literally be trying to get to know this person intellectually. So I would tell you, if you want to get past the first day, like don’t talk about anything physical, like literally like like, that’s just not, that’s not you can you can say, you know, I don’t really want to talk about that. I want to get to know who you are. And not just what we can do for each other physically. That’s just not who I am as a man this, it does. How

Damona  41:01  

you could say oh, you know, a gentleman never kisses and tells. Because she also, she also wants to know like, if she is intimate with you She doesn’t know you’re a virgin she wants to know you’re not going to go and spread her business in the street but

Jack A Daniels  41:14  

isn’t that attractive to a woman like she can you can be my first you could you can show me everything I need to know about sex about love. Is it not attractive to a woman? I don’t get it. Like for me, and that’s what that’s you know, we, you know,

Jack A Daniels  41:34  

I think women I think women

Jack A Daniels  41:38  

look for experience sometimes because it’s, it’s a little harder to meet our needs in the bedroom sometimes, but you can instruct me you literally can tell me everything because I don’t know. This is my first time. You can tell me everything I need to know.

Jack A Daniels  41:54  

Like that. I will say yes, that is hot.

Jack A Daniels  41:58  

Like why we’re women’s What? That’s what you say D, you say, Look, I’m looking for a teacher. I’m looking for an instructor to show me everything that I need to know about sex.

Jack A Daniels  42:09  

I think a lot of women would be turned on by that. Actually, she come back.

Damona  42:15  

All right, we have time for one more question. JACK. This one comes to us from Lisa. She says I’m curious after how many dates? Should you have the are we exclusive talk? We get this question a lot. But I don’t get the answers from you very often. So I want to know what you think.

Jack A Daniels  42:32  

This exclusivity thing um,

Jack A Daniels  42:36  

I just like I believe clarity reduces the clutter in your life. I do totally believe that. I don’t think there’s a number that you can put on it. What I think is there has to be a plan that’s put in place, meaning that we have to be clear and upfront and intentional about what it is that we’re doing. So if you’re going into this and you’re thinking like in between the two Three to five range or the, you know, five to 10 range. You know, I get, once we get on 10 dates or whatever, we’re exclusive. No, be up front and say what it is that you actually want. From the beginning to say, you know, I’m not sleeping around. I’m not dating around. I’m really looking to be involved with something that’s meaningful. It doesn’t mean you have to say that on first date, because you probably won’t get a second.

Damona  43:28  

But let’s say on a first date, I’m I am dating for a relationship. Yeah, I think a lot of people don’t say, dating. Yeah,

Jack A Daniels  43:36  

I’m at on purpose. And I don’t think that Yeah, people are frivolous with it. They just kind of like, walk through and like, I’ll see what happens.

Damona  43:45  

Well, we’re afraid of the rejection. If we say what we really feel and what we really want and they don’t want that or they’re not sure then we’ll get pushed away.

Jack A Daniels  43:54  

Which may happen but men love to be respected. We love respect in every city. And for you to tell me what you want upfront. I respect you. Like, I may not want it the same way that you wanted, but I respect you. And if you’re really going to gain a man’s heart, you have to gain his respect. That is

Damona  44:19  

so true. I respect you so much jack daniels, I am so glad you’re able to join us to to to talk about what’s going on in dating relationships in the last five years since we filmed the TV show hashtag black love. You are getting Oh, oh, you’re you’re and you’re about to have three, three girls. So watch how old you get if you had any hair. It’d be all gray.

Jack A Daniels  44:48  

I miss you jack. I’m so glad to have you on the show. I hope you will come back again and share your wisdom with us anytime. Just make call.

Damona  44:57  

Thank you and jag is here for you. Well, you can find out more about his projects at jack daniels.tv and then get in with the good Tell, tell them the website to get in the database again.

Jack A Daniels  45:12  

So you go to good men.tv join the list, get in a database is going to be epic. The doors will probably open back up in April. So you really want to be on the list.

Damona  45:25  

Get on the list y’all. I hope you enjoyed Episode 299 of dates and mates. I am at damona Hoffman on all the socials. And as I said in the last segment, if you have a question, I want to hear it you can DM me or email me through the website dates and mates calm. And if you love this segment and you get a lot of value out of it. Why not submit a question so we can help you but also helps so many others who are going through the same thing that you’re experiencing? Next week we’ll be doing a masterclass on the future of dating and relationship. And this will be dead it our 300th episode I’m so excited to have you join me for that I cannot wait to do a little future predictions on where we are heading in the world of love. Until next week. I wish you happy dating

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