What Matchmakers Want You To Know About Dating In Your Twenties

What Matchmakers Want You To Know About Dating In Your Twenties


As a sex and relationships writer, I often rehash my dating experiences as a way to say, “Don’t worry. I’ve been there.” While many think this means I’m some kind of love expert, I’m not. At all.

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Caitlin Bergstein and Andrea Leiser, on the other hand, could be described precisely as love experts. They make an actual living coaching people in the art of finding love.

Both Bergstein and Leiser are Boston-based dating coaches and matchmakers, and they work for the full-service matchmaking company Three Day Rule. So who better to ask for love and dating advice than two women who dish it out on the daily?

Dating in your early 20s can and should be fun — it’s a great time to be single. But it can also be confusing (and totally heartbreaking) if you’re looking for a committed relationship while the person you’re dating is still in the process of seeing where it goes with you — and about three or four other people at the same time.

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Thankfully, Bergstein and Leiser gave AwesomenessTV some really great advice on the best ways to approach dating in your early 20s. As you’ll quickly find out, it’s all about staying true to you.

Have an open mind.

Consider potential dates who are slightly outside of your “type.”

“There are many fantastic people in their 20s that are overlooked for lots of reasons, but one that comes up a lot is the fear of how that relationship will be seen or perceived by others,” Bergstein says.

So do your best to not get wrapped up in what other people may (or may not) think, and focus on getting to know a new person who you have some things in common with.

Know what kind of dater you are.

“I’m super outgoing and I personally never felt a connection with my online dates,” Leiser says. “So instead, I put my effort into going out and meeting people rather than spending time swiping for guys.”

But just because online dating doesn’t work for her, she wants to make it perfectly clear that it doesn’t mean it won’t work for you.

“Online dating definitely does work,” she says. “Many of my best friends (including my mom!) met partners online. But if you don’t like it, find dates in a way that feels authentic to you!”

Understand that chemistry can grow and change over time.

You don’t need to feel that all-consuming passion when you first lock eyes with someone to know that it’s going to be a good relationship. Having that spark and attraction for your partner is important, but solid and happy relationships don’t necessarily have to start from there.

As Bergstein says, “My boyfriend and I met in high school. After graduation, we went to different colleges and grad schools (him in Pennsylvania, me in Florida) but kept in touch and stayed friends throughout.”

She continued, “For 14 years, neither of us viewed the other romantically. In fact, when our friends started to question our relationship a few years ago, we both vehemently denied that even the possibility of a romantic connection existed. We maintained that it was JUST a friendship until suddenly it was more. Eventually, we admitted that somewhere along the way (and without us even realizing it) the chemistry that had kept our friendship together for so long had evolved and grown into something more. It took different life experiences and a lot of maturing to get there, but it does happen!”


Get out there. 

“Lots of people tell me it’s hard to find great single people,” Leiser says. “The problem is, they go to the same coffee shop, to the same gym, and to the same bar every day!”

Let’s be real for a second: If you go to the same places all the time, chances are you’re going to see the same people all the time. If you like someone you constantly see, that’s totally fine. But if you’re finding that there’s nobody good to date, it might be time for a change of scenery.

You don’t have to completely turn your life around to meet new people. But just walk your dog on a new route, go work or study in a different coffee shop, or try the new yoga studio that opened up. That way you’ll increase the number of people you run into every day.

Think about qualities that are most important to you.

It can be a really daunting task to figure out what is most important to you in a partner, Bergstein says, but a great way to figure this out is to think about how you would describe your friends to a stranger. Yes, your friends.

“Oftentimes, people are drawn to similar values in friendships as they are in romantic relationships, so by examining the people you surround yourself with, you’ll be able to identify those things that are the most important in a partner,” says Bergstein.

Some really good things to look out for are:

  • How someone treats their family, friends, and strangers. This can be a good indication of how they’ll treat you once the “honeymoon phase” wears off.
  • How someone reacts to your goals, hopes, and dreams. Not everyone will understand another person’s life goals or dreams, but how they react to them is huge. Are they supportive and encouraging, or do they point out how unrealistic or unlikely they are?
  • How someone responds to conflict. Unfortunately, conflict is inevitable in every relationship. So keep an eye out for someone who shuts down in normal, day-to-day uncomfortable situations or conflicts. That may be a sign they have trouble communicating or discussing tough issues.

Be completely authentic to who you are.

When you’re being your true self, you’ll feel much more confident on dates.

“Someone once told my friend to always wear high heels on dates, but my friend absolutely hated them,” Leiser says. “I encouraged her to do what made her feel sexy. That meant wearing a sexy top.” So do what makes you feel awesome and you’ll be your best self on dates.

It’s okay to be single. Seriously.

“Throughout college, I dated but had very few actual relationships while most of my friends were almost always in serious ones,” Bergstein says. “Being the only single one, it was all too easy for me to compare my love life to theirs, which often led me to wonder what was wrong with me. Looking back, I know that I wasn’t ready for a relationship and didn’t really want to be in one. I was focused on school, my friendships, and figuring out what I wanted out of life.”

It’s okay to be single and comfortable with it. Just own it.



Kristine Fellizar
Kristine Fellizar

Kristine Fellizar is a writer and editor based in Los Angeles. She specializes in everything related to sex, dating, and relationships. When she’s not working and feeding into her coffee and boba addiction all over L.A., chances are you'll find her at Disneyland.