Successful relationships thrive on compatibility, vulnerability and intimacy. But, talking to your partner about your finances can be downright scary.

Don’t worry. Financial therapist Amanda Clayman is here to put your fears to rest. She’ll illuminate how money fears show up in dating and relationships and give us the tools to have a healthier outlook on finances for ourselves and our partners.

DATING DISH (1:30)

(1:30) Feel like something is missing? Maybe it’s time for a “reset relationship”:

Stylist magazine suggests that a “reset relationship” could help you rediscover the spark you’ve been missing. According to the article, it turns out that a lot of us want to make what they call big life changes, such as quitting a job and ending a relationship. In fact, a new study from Bumble and Plenty of Fish said that almost half of single people are craving a reset in their dating life, and 72% desire for life to change significantly rather than go back to how it was before COVID 19.

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So what is a relationship reset? Basically, It’s a relationship that is all about serving your own need to refresh your life and get yourself out of a funk. It’s not that different from a rebound relationship (except in this case, you’re rebounding from this pandemic). But Stylist mentions how reset relationships aren’t only a pandemic phenomenon – rather that they actually can happen at any time in your life when you feel stuck. 

If you’re thinking about diving into a reset relationship of your own, Damona suggests that you don’t look at it as a temporary thing. Look at it as a mindset shift that is potentially going to change the entire trajectory of your life. Now, don’t get panicked. This sounds like a lot, but you can make these changes in small incremental steps. For instance, try opening up your search preferences in your dating app to include qualities you hadn’t thought about before. After all, to go someplace mentally that we’ve never been, we have to do something we’ve never done (or date someone we never thought we’d be open to).

Another way you can prep for your reset relationship is to question the rules and requirements you’ve made for the people you’re dating. Who wrote these rules? Did you write these rules? Did society write these rules? Do these rules still apply to you? Really focus on your must haves and deal breakers, and look at them through the lens of your future. Because maybe if you explored a little bit more, that reset in your dating life could lead to a tremendous reset in the way that you live the rest of your life.

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Are you looking for your reset relationship? Then maybe you need the Profile Starter Kit to get you online easily, and moving forward in your dating success story. 

Download yours for free here.

 

AMANDA CLAYMAN (9:09)

Damona is so excited to welcome financial therapist Amanda Clayman! Amanda specializes in the cognitive, emotional, and behavioral aspects of our financial well-being (hence, financial therapist). 

She is the host of the recurring Death, Sex & Money podcast series Financial Therapy with Amanda Clayman, and authored several financial wellness courses for LinkedIn Learning. Amanda’s advice has been featured in CNBC, Fox News, The New York Times, The Wall Street Journal, REAL SIMPLE, Forbes, and more.

Amanda’s passion for financial wellness began with a dramatic styling mishap, which she will share with Dates & Mates listeners today. 

(11:00) Universal financial red flags:

Damona mentions how she’s received the question from a client, if she should date someone with significant debt. Amanda brings up the idea that for some people, if a potential partner does have debt, that makes them feel incredibly vulnerable about their own security – “and anything that makes us feel vulnerable is obviously our business and something that we can set boundaries around.” Although Amanda declares having significant debt isn’t universally a red flag on its own, it might be a red flag or deal breaker for some based on their own relationship with financial vulnerability.

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Damona inquires if there are any universal red flags, and Amanda responds: “When I think about red flags, I think about them more in terms of process… like if a person is really secretive and they won’t disclose things even when you ask them to, that’s a red flag for me. Because that shows me something about how that person is going to be open to the kind of partnership that I have in mind for my potential mate.” Amanda also adds how someone who won’t engage with you and discuss both your needs and wants around money is definitely a red flag – communication is key.

(13:13) What does it mean when you’re withholding spending money?: 

Damona brings up a story about a friend of hers who grew up with money and a stable job, but weirdly enough was always so insecure about her spending. Damona continues to ask, what does it signify to have extreme frugality with money? “So I love in the example with your friend, the characterization [you used] was that something was outside of her comfort zone, or that everything it seemed like was outside of her comfort zone. And so she was bringing in this kind of anxious intensity to what maybe should have been a simpler choice… And absolutely, this is where our inner set of experiences and sort of strategies that make sense to us [come into play], where sometimes it feels like our insides are not quite matching the outside.”  

Amanda uses the quality of frugality as a specific example. She describes how we can differentiate between frugality being a strategy (i.e. being really careful with your means and your resources and a way of paying extra close attention), or we can think of frugality as a rigid behavior (i.e. where the caution is not matching the circumstances). But for the person inside of the behavior, frugality may have a totally other purpose. For example, Amanda describes how people who foster a high degree of control in their financial lives do so because they think control is the antidote (most likely for anxiety). So if someone has significant anxiety, then exerting control in their finances is sort of a continuous loop in that person’s mind – and that’s being expressed in their relationship with money.

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(15:46) Self-indulgence & money:

Have you ever experienced guilt over treating yourself to something you knew you didn’t need? Or tried to buy something self-care oriented, only to counterintuitively feel like you were indulging yourself? Amanda addresses this anxiety – “What I would like to say to everyone is that we all have money ‘stuff’. So I think stepping back and being like, this is all very personal, how do I want money to work for me? Take the decision making into a clear and neutral place.”

When Amanda says ‘neutral place,’ she is speaking to the way we direct our money outside of those times when old stories and old obstacles jump up in the way, and tell us that we can’t or we’re bad or we’re not worth it. Taking your relationship with your finances to a neutral place, if only for a few moments, is where you can engage more neutrally with the tool properties of money, such as organization, allocation and negotiation.  “We can focus on those aspects to try to program self-care into our budget.  We experience ourselves as being able to use money effectively, to nurture, grow, take care of ourselves.”

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(17:15) The $19,000 Haircut:

Amanda’s journey to financial wellness all started with what she poeticizes as a $19,000 haircut. “I took on a lot of my parents’ anxiety about money without knowing it, since my parents had experienced real deprivation in their childhoods… And when they came into adulthood, they always felt like the wolf was at the door…And I didn’t have the ability to know if that was true or not true in terms of danger… But when I got to be a grown up, I noticed that I had a really hard time paying attention to money, that anytime I was trying to look at my cash flow, look at my expenses, even to make a deliberate decision about money, I just couldn’t do it. I would get so triggered by it.”

Amanda persists that because of her financial triggers, she became increasingly impulsive with her spending habits – doing a lot of emotional spending, bouncing checks just to get by, and later moving to New York with nothing in the bank. She says everything came to a head when she asked her mom to give her a (what turned out to be terrible) haircut, because she had bounced a check at her hairdresser and couldn’t go back. 

Damona clarifies, “and you were at that point $19,000 in debt, yes? All of those checks that you were writing finally caught up to you.” Amanda responds, “I look at myself, like who is that person who just moved from Michigan to New York, like it’ll all work out? And the fact is, it did. Financial problems and consequences can be very, very real. But where we can, I think that we should appreciate that there’s a lot of on the job learning when it comes to money.”

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(24:35) The Pillars of Financial Intimacy:

Amanda often speaks to the idea of ‘financial intimacy’ and the Five Pillars that help foster financial intimacy in a relationship. She gives us a rundown of each quality below: 

1. Equality. “Meaning that both partners have equal decision making power.” 
2. Inclusivity. “That means that both partners have to show up to this process, there’s no opting out by one person, there’s no pushing out by the other person.”
3.  Transparency. “This is how we make sure that both partners have access to the information that they need. And it doesn’t mean that we can’t negotiate areas for privacy, but even those areas of privacy still have boundaries. Like we might say, both partners have to agree not to open new accounts without talking to the other person, or any expenditure above a certain point is going to get discussed.”
4.  Flexibility. “Flexibility means that we allow ourselves to change, we allow our decisions to evolve that a level of sort of exposure and vulnerability that may not feel right for you at one period in the relationship, may become more right for you as time goes on… The point is, we can change all of these things, there’s no right or wrong thing that we have to stick to.”
5.  Sustainability. “Sustainability is like, it just has to work enough for both of you. Like if one person is feeling like everything is wonderful, and the other partner is like, ‘I cannot stand to live under this tyranny’. Your money may look okay, but trust me – that is showing up somewhere else in the relationship.”

 

Connect with Amanda on IG @amandaclayman, or visit her website to learn more about private coaching and courses.

 

DEAR DAMONA (31:45)

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

• VIP Question from D – What are the rules of thumb for continuing a conversation after the person takes a long time to respond back? For example, I finally got a response to a basic message that I sent this past June. Should I respond right away or should I wait a few days? I’ve also had people respond back recently after I sent an initial message… in 2019. I’ve also had a person respond to my initial message, then ghost me for about a year, start talking again and then ghost me again. Any suggestions?

DAMONA’S DEALS

• Download the OkCupid Dating App for free today!
• Click here to try Damona’s free First Date Starter Kit!

I don’t know about you, but lately it’s been feeling like love is in the air. Spring is here, the flowers are blooming, we’re doing all our spring cleaning… so why not also think of spring cleaning your dating wardrobe?

If you’ve never thought about having a dating wardrobe, you’re in luck. Damona’s guest today, Stephanie-Gisondi Little (also known as the “fashion therapist”) will tell you why it’s so important and how to create one – even if you’re on a budget.

DATING DISH (2:30)

(2:30) Feeling disorganized in your love life?:

We’ve all heard of attachment styles, right? Well Allure Magazine explains in this article how disorganized attachment became the most misunderstood (and forgotten) attachment style. If you’re not familiar with attachment theory, it’s a method of analyzing and understanding how our childhood influences our relationships in adulthood. There are three primary attachment styles that are most often utilized by mental health professionals – secure, anxious and avoidant. And when you don’t fall under any of those categories, that’s where disorganized attachment comes in.

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According to professionals in the article, about 20-40% of adults have a disorganized attachment style. It can present itself as fear of abandonment or of getting emotionally close to someone.  In extreme cases, it can emerge when a child grows up in an abusive household, which makes sense – you grow up in chaos, so then you bring chaos to your future relationships. Here are some signs that you may have a disorganized attachment style:

• Anxiety about abandonment or rejection
• Emotional or physical hostility (which shouldn’t be showing up in any relationship)
• Constant mistrust in a partner
• Someone who goes through intense periods of connection and detachment
• Struggling with dysregulation like substance abuse or out of control behaviors
• And if you’re dating someone who sounds a little bit like this, it may be difficult to engage with them because their behavior can feel chaotic or unpredictable.

Damona believes that we move through these attachment styles differently in different relationships. Think about it – different people bring out different elements of your personality, and they trigger different things from your past. So it may not just be about being in a relationship with someone who’s securely attached, or moving towards a secure attachment yourself. You can be multiple things at the same time, as long as you are getting the right support from the right people to help you navigate your behaviors.

(7:03) Could an A.I. predict your relationship red flags?: 

Wouldn’t it be nice if we could have a third POV in our relationships to spot any red flags, before we start to introduce our new partners to friends and family? As it turns out, A.I. (artificial intelligence) technology could be that third POV. This fascinating article in Screenshot Media gives us all the deets on A.I. dating apps. A recent study titled Loving the Age of AI Dating Apps surveyed people on how they would feel about working with an A.I. dating app. Nearly half of the respondents admitted that they would join an advanced A.I. powered dating app if it meant having more chances at finding a long term partner. But when they were asked what they would do if an A.I. dating app did suggest they break up with someone, only 7% said that they would end the relationship immediately.

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Damona is a little skeptical that A.I. could predict the end of a relationship, but believes that it could be used to find better matches for the participant overall. Honestly, so many of our behaviors that we think are random, are actually more predictable and pattern-based than we realize. According to the article, the main input that the A.I. would use to determine the success of your relationship, was your in-app user behavior – conversations with matches that had gone silent, changes in conversation based on keywords, and frequency of conversations. And if the A.I. could recognize when you acted in a way that could potentially threaten the relationship, they might be able to tell you in advance.

Now of course, there’s always issues, right? With A.I., it would be difficult to know what information to feed the A.I. from outside the app to get a strong enough understanding of the relationship. So basically, folks, we’re not there yet. But there is even more potential as to how an A.I. could predict your best matches before you have even had a conversation. Using A.I. in dating apps is only a proposal at this point, but I suppose only time will tell which direction dating app technology will be heading in next…

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STEPHANIE GISONDI-LITTLE (13:25)

Damona is thrilled to welcome Stephanie Gisondi-Little, the Fashion therapist, to the Dates & Mates family!

Stephanie began her career in the fashion industry working between New York and LA, with top designers like Emanuel Ungaro and Nicole Miller. Her advice has been featured in Marie Claire, In Style, The Hollywood Reporter, and more. 

Stephanie also works to style clients and their closets from many different backgrounds, warranting her the title of ‘fashion therapist.’

(14:00) Why are you the ‘fashion therapist’?:

First things first, why does Stephanie call herself a fashion therapist? “I call myself a fashion therapist because having worked in retail wholesale garment industry, and having had my own ecommerce website, I realized that it’s not just about clothes at all right? The clothes are the fun part. But it’s really about how the clothes make you feel. In addition to being a personal stylist, I also work as a wardrobe organizer and closet organizer. And when you see how difficult it is for people to let go of certain things, the reasons why we hang on to them, you start to see that it’s just it really is about so much more than just clothes. And there’s a lot of emotional stuff that goes with just getting dressed.” 

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Stephanie believes that clothes are a tool to express our core essence, and a great way to start conversations. She also recognizes the stigma around clothes only being about fashion, but there are trends for every body and every budget. “The thing that I realized is that you can either love clothes, or you hate clothes. But in our society, one has to get dressed, right? So the best thing to do is to figure out what works for you.” 

(16:55) How to prep for the occasion:

Damona asks Stephanie, when prepping for a date or an event, what are the questions we should be asking ourselves? “I think the first question to ask yourself is, what time is it happening, where is it happening, and how do you want to show up as your favorite self?” And your favorite self for going on a first date may be a different self than the one that gets dressed for a business meeting or a wedding. Stephanie suggests looking into the kind of feeling you want to have. Maybe you want to feel more armored up, so you wear a motorcycle jacket or padded shoulders. Or maybe you want to feel more free and flowey, so you choose to wear that sundress you always get complimented on or a certain kind of fabric. But regardless of how you dress, make sure that your attire is appropriate to the time and location, and that you wear something clean. This is a big one for Stephanie, because even if you don’t have the fanciest outfit, showing up in stainless clothes and looking polished shows that you have respect for yourself, and respect for the person that you’re showing up to meet. That can’t be bad for a first impression, right?

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(20:06) Dress how you want to be perceived:

Damona mentions her strong belief in presenting yourself the way that you want to be seen. Particularly in dating profile photos, people are developing an impression of who you are in a split second based on the way that you’re presenting. Stephanie adds, “I take it back to the cave brain, where we are hardwired to be kind of on alert to say ‘are you from my tribe or are you not from my tribe?’ So we are making these instantaneous micro decisions. And for better or worse, they do affect what people think of us.” We don’t have control over a lot of things that happen to us in life. But one of the things we can control, and have a surprisingly large amount of control over, is how we are perceived. “I always say we all have multiple facets to our personalities and thank goodness your wardrobe can and maybe should reflect that.” 

In terms of first dates, having a couple of go-to pieces for how you want to make a first impression is a great strategy. “It’s nice to know that you have at least one thing that fits you, feels like you like your current self, and you’re physically comfortable in it. What you don’t want to be doing is sitting around adjusting your bra straps, or thinking ‘my feet are killing me in these shoes’ or ‘this shirt makes me sweat buckets.’ You know, that’s not a cute feeling to be having while you’re trying to make nice conversation and get to know somebody.” Damona adds that so much energy already goes into preparing for dates emotionally and mentally, so having your wardrobe already decided helps to set you up for success even more so.

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(24:15) Stay adaptable:

Damona continues with something some people often have a hard time doing, which is staying flexible in your wardrobe – our wardrobes evolve just as we evolve over time. So keeping those pieces of “aspirational clothing” in your closet, i.e. clothes that you keep because one day you’ll be able to fit into them again, actually takes up more mental energy than we realize (not to mention closet space). Stephanie hits Damona with one of her favorite facts – “The average person makes 10,000 micro decisions every day. We’re not thinking about all of them, but we’re doing them. So there is energy that you’re expending before you’re even out the door if you’re looking into a closet that is not seasonally appropriate.”

Stephanie agrees that we all evolve in life, so having a closet that is equally as adaptable matters. “It’s worth populating what you have with one or two fresh things [every so often], even if you have a uniform of a kind that you wear all the time… If you can look around and say, ‘what’s one piece that’s on trend that I think would feel comfortable or look good on me,’ just try something! Whether it’s a brighter color or shoe style or what have you. There’s just so many ways to kind of pop what you already own.”

(27:28) Enclothed cognition:

Stephanie shares with Damona a concept in social psychology called “enclothed cognition,” which essentially states that you become what you wear. “I think we all instinctively know that when we get dressed, we get called for an interview, or a first date, you dress differently. And it makes a huge difference, what you feel once you start to get intentional in thinking about that. Damona remarks that you can also change the way you feel based on what you wear under your clothes, and this may even have a stronger effect since the undergarments you wear would only be for you.

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Damona mentions that tailoring is also a tool to help you feel your best in your clothing, and even take a piece that you may have felt frumpy into feeling like a completely different person. Stephanie states, “Totally agree. I think we’re all fed this continual diet of how everything should fit perfectly, and it should just be easy, breezy… And the other thing to bear in mind is that you know one brand’s 8 is another brand’s 10 is another brand’s 12.”

(33:11) Having a dating capsule wardrobe:

If you’ve never heard the term before, a “capsule wardrobe” is a small collection of clothing items designed to be worn together which are synchronized in color and line. The main point of a capsule wardrobe is to be able to have many outfit options without needing an excess of garments. So if you’ve never thought about creating a capsule wardrobe exclusively for dating, this may be a game-changing move for you. Stephanie gives some tips on how to get the most out of your dating collection. 

“I recommend getting better quality wherever possible. You can get that more easily these days second hand, in very good condition. And it’s a little easier to source because there are so many great places… But I would rather have fewer pieces of better quality.” She recommends checking out classic pieces such as a well-fitting blazer, black ballet flats, a good white t-shirt, and a good pair of jeans. For men, she even recommends extending your capsule wardrobe by using the jacket from a 2-piece suit as its own blazer. Damona also points out that red is a good color to have somewhere in your capsule wardrobe, because it’s a color that we are biologically predisposed to be attracted to, and it naturally catches our attention.

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When creating your wardrobe for dating, also consider adding some conversation pieces. These are useful for dating because not only can they break awkward silences and inspire conversation, they have a story behind them which you can speak with more passion and presence. This can be anything from jewelry, to a bright red lip, or a cool graphic tee. Fun, printed socks or button-downs are also a great way to set the tone that you are playful and don’t take yourself too seriously. And to top it off, Stephanie adds that comfort is key – “You got to be comfortable. I always like to think, do your outsides match your insides? You know, are you dressed in a way that doesn’t really reflect who you are at all? Maybe you’re dressing too conservatively, and that’s not really who you are inside. Or maybe it’s vice versa? But comfort is key. It shouldn’t be that hard to get around in the clothes. I want folks to be comfortable and have a good time and be able to focus on the things that are far more important than just clothes.”

 

Be sure to follow Stephanie and her company on Instagram at @composed_co. 

If you’re interested in learning more about fashion therapy, you can work with Stephanie virtually or in person through her website https://composedco.com/. 

DEAR DAMONA (42:20)

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

• Email from H – Do you have any suggestions on how to deal with the societal pressure to find someone? As a single guy in my mid-twenties, I’ve felt behind in finding a partner. This feeling is amplified whenever I see my friends enter or maintain long term relationships and even get engaged or married. I know that this thought is completely false, and that I can develop a satisfying long-term relationship at any age. I just struggle with feeling like I need to achieve this milestone ASAP.

• Email from T – For online dating, do you have any tips to get a guy to ask you questions? When I’m on dating apps, I feel like I’m the person always asking the questions and moving the conversation forward. I would like for the guy to ask me questions too.

 

DAMONA’S DEALS

• Download the OkCupid Dating App for free today!
• Click here to try Damona’s free First Date Starter Kit!