7 Things Matchmakers Want You To Know About Dating In Your 20s

by Kate Edwards

At 31, I've been dating for a solid 15 years. Sometimes, I'd have four first dates in a week. Other times, I'd be in pseudo-serious relationships. But one thing was consistent: I made a lot of mistakes.

I don't mean real mistakes, like going to jail or hitchhiking to Mexico with an axe murderer. But I did make the type of mistakes that make me cringe a bit when I remember them.

My dating mistakes are my metaphorical neon tube tops and scrunchies. I simply look back and think “Why?” I don't regret anything, of course. Each mistake taught me something about myself and what I was looking for in a partner.

But I do wish I could go back in time and teach myself a few lessons, Marty McFly style. Now, I work as a dating expert and matchmaker, so I've learned these lessons on a much bigger scale. My clients thank me, and so will you:

1. Don't sleep with him too soon.

My mother, who was actually quite progressive, told me not to sleep with men too soon. “They'll respect you more” is the resounding chorus heard from the older generation.

When you're in your 20s, you reject conservative values. You rebel against the norms. Hence, you can end up sleeping with guys pretty soon after you meet them.

But here's the thing: A lot of young men want what they can't have, and sex is the biggest example of this principle. Please take my word for it.

2. Stay away from the ones who are off-limits.

That guy who sits on the other side of your cubicle, your best friend's ex, your married boss, anyone married: Don't do it. At some point, every woman is faced with a potential suitor who is notedly off-limits.

You lie awake at night, thinking about what it would be like, and there's just something about him that intrigues you. You tell yourself this situation is different from every other office romance or affair. You justify your actions with lies. Let me save you the heartache: Off-limits love is rarely worth it.

That intrigue you're feeling? You're just attracted to him because he's off-limits, not because he's the one for you. As soon as the dust settles, one of you will no longer be interested.

Dating is hard enough. Don't make it harder by going after the inaccessible.

3. It's way easier to make your own money.

In my 20s in New York, I had two types of girlfriends: the type who worked hard on their careers, and the type who worked hard on their diets and makeup in order to attract wealthy men.

Sure, both were well-intentioned investment plans. Both seemed to take a lot of effort.

Over the years, I saw my banker and ad exec girlfriends climbing the corporate ladder, pulling long hours and paying their dues. Meanwhile, my model-esque friends were living more lavish lives. They were being taken out by rich men, and getting married to the best-looking highest bidder.

It seemed like those women were winning. But as time went on, the power began to shift. My friends who worked hard ended up finding love as well. But instead of marrying men who loved their looks, they married men who loved their minds and ambition.

That's when I realized that when you make your own way, love follows. When you follow the money, you'll eventually have to find your own way. After all, you're going to spend 60 years with this person. Someone who makes you laugh will always take you farther than a fancy car will.

4. You're going to end up with different people than your friends will.

Just because your bestie ends up with a Harvard hedge fund manager, that doesn't mean you have to as well. It doesn't mean she did better than you.

Trust me: The further you get away from college, the less it matters where someone went to school. As I've discussed before, oftentimes, the men who love you the most aren't the ones who look best on paper.

Stop comparing your love life to your friends'. Don't get so caught up in who you're supposed to end up with. When a female friend asks me if I like her significant other, I now say ,“Well, I wouldn't marry him.” When she looks at me like I just insulted her, I say, “Wouldn't it be weird if I wanted to marry your boyfriend?”

We should appreciate that everyone is attracted to different things, shouldn't we?

5. Once a cheater, always a cheater.

I've been dating for 15 years, and I have yet to find an exception to this rule.

6. Give the good guys a shot.

When I think back at all the dates I've been on, I realize that I – like most women in their 20s – overlooked the ones who were just plain nice. I wanted someone with an edge, or someone who was the best of the best.

I didn't want to waste my time with someone who I didn't think was "the one" for whatever reason I made up, like weird hair, ugly apartment, didn't catch that foul ball. But now, I know I had no idea what I wanted back then.

I didn't take the time to get to know people because I believed they didn't fit my mold. I've seen so many men get brushed off quickly because they were seen as “too nice” or “not perfect.” Those are the ones who ended up making the best husbands and fathers.

When you're 30, you can see that. When you're 23, you just see them as duds. Give the nice guys your time because they are much harder to find later on.

7. There is no timeline.

When I was 17, I thought I would be married by 24 and have kids by 28, just like my mom was. As I approached 28, I realized my timeline had gone out the window. But instead of acknowledging there is no such thing as a timeline when it comes to dating, I replaced my old timeline with a new one: I'd be married by 30 and have kids by 34.

I even got engaged to the wrong person in the hopes of making this new timeline work. But I was wrong.

At 29, I had to start all over again. But this time, I decided to throw out the timeline and just enjoy the ride. Unsurprisingly, I've now found the best guy yet.

Looking back, I'm glad I didn't get married at 23. I wouldn't have been able to travel alone through Europe or go back to get my MBA on a whim. Timelines are like tan lines: Having them there makes you feel better about yourself. But not having them there at all feels a million times better.

As a matchmaker, I've heard so many stories, and I've been able to learn more about dating than my age would suggest. Here's the best hint of all: Your 30s are going to be your best years yet.