A 4th Generation Matchmaker’s Tried-and-True Dating Tips

What happens when 60% of the single population thinks swiping while watching Netflix counts as putting yourself out there?

This week’s Dates & Mates guest, fourth-generation Matchmaker Maria, dropped some hard truths that might sting a little. 

Her new book “Ask A Matchmaker” has already gotten hundreds of people into relationships in just four months. That’s because she’s not here to sugarcoat the reality of modern dating.

When Maria says “a lot of people are participating in dating by laying on their couch and swiping on profiles while a rerun of The Office is playing in the background,” she’s talking about most of us. But here’s the thing: this isolation isn’t entirely our fault.

We’ve accidentally designed a society that cuts us off from the natural ways humans used to meet. And it’s costing us connections we desperately need.

(00:02:20) Meet the Fourth-Generation Matchmaker Who’s Seen It All

Maria’s family has been bringing people together since before dating apps existed. Her great-grandmother was a matchmaker. Her in-laws met through a matchmaker in 1976. Her parents met at a friend’s party in 1983 without one.

Now she’s putting 15 years of matchmaking wisdom into her brand new book, “Ask A Matchmaker: Matchmaker Maria’s No-Nonsense Guide to Finding Love.” In just four months since release, it’s already gotten hundreds of people into relationships because Maria doesn’t sugarcoat the hard truths about modern dating.

That seven-year gap between her parents and in-laws tells the whole story of how we got here. “Even when you get away from arranged marriages,” Maria explains, “people were meddling in their lives. With my in-laws, their parents were involved. The neighbors knew about it. The cousins had opinions.”

Her parents’ “love marriage” still had community support. Friends arranged group outings. People called the same mutual friend for intel. There was gossip, opinions, and awareness of shared values.

That’s what we lost: the village that used to meddle in your love life.

(00:05:58) Why You’re Dating Alone (And Why That’s the Problem)

The majority of single people are participating in dating by themselves. Not just physically alone on their couch, but emotionally alone in the process.

“Something like 60, 70, 80% of people are online dating,” Maria notes. “I say in the book, don’t think of it as a dating app. Think of it as a meetup app.”

But we’ve created what Damona calls “siloization” in every part of our lives. You can’t call someone without permission. You can’t drop by a neighbor’s house. Your windows are up, your air conditioning is on, and nobody’s walking by to say hello.

The nuclear family became the only family that mattered. Meanwhile, every other Western nation still has grandparents, cousins, aunts, and uncles living on the same street.

We’ve optimized for convenience and privacy, but we accidentally optimized out connection.

(00:18:33) Your Algorithm Is Making You Lonelier

Here’s something that will make you uncomfortable: ask your friends to show you their Instagram explore pages next time you’re out together.

Most people won’t do it. It’s literally the most intimate thing you could ask for. And that algorithm is feeding everyone the most extreme viewpoints possible, creating silos of beliefs that keep us isolated.

You’re taking in stories from Instagram, TikTok, rom-coms, and fairytales without realizing what diet you’ve fed yourself. Then you operate from those beliefs, making assumptions about people based on political affiliation or lifestyle choices without ever getting to know them.

(00:24:34) The Five Pillars That Actually Predict Relationship Success

Forget “tall, dark, and handsome.” After 15 years of matchmaking, Maria has identified what actually matters: physical, spiritual, intellectual, emotional, and financial compatibility.

Physical isn’t just attraction—it’s safety and respect. Men assess attraction in four seconds. Women assess safety. Both happen in the first 40 seconds of meeting.

Spiritual is soul connection, not religion. “Do you feel a connection? Were you meant to meet this person in this lifetime? You can tell this by the end of the first date.”

The last three keep relationships going long-term. Intellectual means shared humor and growth, not degrees. Emotional covers self-awareness and conflict resolution. Financial is about lifestyle and values around money, not income.

“When you go through the book, it’s very introspective. It’s deeply personal to the reader,” Maria explains. You write down what’s ping-ponging in your head and get clarity on who you’re actually meant to be with.

(00:33:30) Why Deep Text Conversations Count for Nothing

Maria’s famous 12-date rule has gotten thousands of people engaged. Wait 12 dates before becoming intimate, but here’s the catch: she defines what counts as a date:

• A phone call, video call, or in-person date lasting a minimum of 20 minutes, maximum 3 hours. 
• You can have two dates in one day. 
• Three out of 12 dates must be in-person. 
• Most people complete it in two to three weeks.

And before you ask: “Deep text conversations count for nothing. And audio messages count for shit too.”

Why does this work? “You’ve now given yourself a challenge to intentionally get to know someone,” Maria says. You’re looking for four things: how they act on their bad days, their good days, your bad days, and most importantly, YOUR good days.

You discover a lot about someone when you’re not thinking about having sex with them.

📲 Connect with Matchmaker Maria

Get the book Ask a Matchmaker by Matchmaker Maria

Connect with Maria on Instagram. Facebook, and TikTok

💌 Got a communication question you’ve been sitting on?

Whether it’s about dating, relationships, boundaries, or what the heck to text back… Damona’s here for all of it.

Send your question in a DM or voice memo on  Instagram, TikTok, or Facebook, or send a voicemail or text to 424-246-6255. It might just be featured in an upcoming Dear Damona segment.

And remember: Dates & Mates isn’t just about romantic relationships anymore. It’s about the people who matter most: partners, friends, family, and you.

📝 Want a better way to track what’s working (and what’s not) in your love life?

Get your free Date Tracker at damonahoffman.com/datetracker