What I Wish I Knew When I Was Dating in My 20s: Lessons & Mistakes

(Originally published on Elite Daily)

At 31, I’ve been dating for a solid fifteen years. Sometimes it would be four first dates in a week, and other times I’d be in pseudo-serious relationships, but one thing was consistent – I made a lot of mistakes. Not real mistakes, like going to jail or hitchhiking to Mexico with an axe murderer, but 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 really regret anything, of course, because each mistake taught me something about myself and about what I was looking for in a partner, but I 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.


Don’t sleep with him so 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 and your more reserved friends ad infinitum. But in your twenties, you reject conservative values, you rebel against the norms, and hence, you end up sleeping with guys pretty soon. Maybe it’s not the first date, but it might be the fourth date, and you feel like an empowered feminist, which you are. But here’s the kicker – holding out on sex is not about feminism, and it’s not even about being lady-like. It’s about understanding that young men only want what they can’t have, and trust me, sex is the biggest example of that principle. I can count three men who I would have loved to have dated who dropped me like a bad habit because I slept with them too soon. PLEASE just take my word for it (and that’s all the counting I’ll be doing in this article!).


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, even the most proper 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. The intrigue you’re feeling? You’re just attracted to him because he’s off-limits, not because he’s the one for you. And 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.


It’s way easier to make your own money

In my twenties in New York, I had two types of girlfriends – the type that worked hard on their careers and the type that worked hard on their diets and makeup in order to attract wealthy men. Sure, both were well-intentioned investment plans, and 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, while my modelesque friends were living a more lavish life, 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 had 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. And 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 70 years with this person, and I assure you that someone who makes you laugh will take you farther than a fancy car.


You’re going to end up with different people than your friends

Just because your bestie ends up with a Harvard hedge fund manager doesn’t mean you have to too. And it doesn’t mean she did better than you. Trust me, the farther away you get from college, the less where someone goes to school matters, and as I’ve discussed before, oftentimes the men who love you the most aren’t the ones who look the best on paper. Stop comparing your love life to your friends’ and don’t get so caught up in who you’re supposed to end up with. When someone asks me if I like their significant other, I now say “Well, I wouldn’t marry him!” When they look at me like I just insulted them, I say, “because wouldn’t it be weird if I wanted to marry your boyfriend?” We should appreciate that everyone is attracted to something slightly different, shouldn’t we?


Once a cheater, always a cheater

I’ve been dating for fifteen years and have yet to find an exception to this rule, despite making plenty of excuses along the way.


Give the good guys a shot

When I think back at all the dates I went on, I realize that I, like most women in their twenties, overlooked the ones that 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. But now I know that I had no idea what I wanted back then. I didn’t take the time to get to know people because they didn’t fit my mold. I’ve seen so many men brushed off quickly because they were seen as “too nice” or “not perfect,” and those are the ones who make 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 the time of day, because they are much harder to find later on.


There is no timeline

When I was 17, I thought I would be married by 23 and have kids by 28, just like my mom. As I approached 28, I realized my timeline had gone out the window. But instead of acknowledging that 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 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 enjoy the ride. And not surprisingly, I’ve now found the best guy yet. Looking back, I’m glad I didn’t get married at 23. I wouldn’t have traveled alone through Europe or gone back to get my MBA on a whim. Timelines are like tanlines – 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 thirties are your best years yet.
by Kate Edwards

Dating Expert

Kate Edwards, Three Day Rule Matchmaker and Dating Expert

Leave a Reply

Your email address will not be published. Required fields are marked *