9 Surprising Things I’ve Learned About Dating After Having Over 100 First Dates

Next week, I’ll turn 27, and my most recent worth-noting relationship ended a few days after I turned 23. That’s right: four years of going on just about every type of date you could imagine.

Up until recently, I was on all of the dating apps. I’ve met with matchmakers, I’ve gone to speed dating events, group dating, dating meet-and-greets based on interest … and so much more. Honestly, if you named it, I’ve likely tried it.

I haven’t kept track on an exact number, but I’ve gone on at least 100 first dates, if not more, in the past four years. They don’t phase me too much; after you’ve been out so many times, they all start to blend together. A handful turned into six-week to two-month things that weren’t quite significant relationships but weren’t casual, either.

As much as it discourages me to admit, I haven’t had much luck dating in my 20s, but I’ve learned so much about myself, about men, about what I want, about (the lack of) romance, and about what I hope for my future.

Between the good, the awesome, the terrible, the intoxicated, the inspiring, the skivvy, and everything in between, here’s what going on 100 first dates have taught me:

1. We all absolutely want love.

It’s really easy to say that the only thing men want is sex. It’s easier to call them all scumbags who are always looking for the next big thing instead of giving a second glance. I could be bitter about it, and at times I am, but I try to remember that ultimately, most of us have the same shared goal: love.

Guys complain about bad dating experiences and stories of unrequited love, just like we do. I hate when people tell me that “when it works, it just does!” But they’re right; it’s less about the number of dates you have to endure and more about the one that actually make the cut.

2. You can’t trust a damn word a guy says on the first date.

And no, not because he could be a liar who’s dishing on the smooth talk of seduction. I can’t tell you how many men on the first and second dates have talked about the future like it’s a guaranteed path we’re starting. Men have talked about this wedding they have in a few months and how fun it’d be for me to join them; others have mentioned how our hometowns are so close that we could do the holidays easily and visit both families.

Men dream about the future just like we do, and sometimes they have a bad case of fantasy vomit right from the get-go. Those statements and plans mean nothing if there isn’t a follow-up, so don’t get your hopes up.

3. There are no first date “rules” EXCEPT: Put your iPhone down.

Though I write about dating pretty frequently, I never click on those articles that tell you exactly when, where, why, and how to text someone after you’ve had a great date. The temptation is always — always! — there to reach out because you really want to see if that first encounter has the possibility to be more.

And though every relationship is different and there’s no set-in-stone rule of thumb you should follow, generally speaking, men who are interested in you won’t hesitate to reach out. In fact,
I’ve found the ones who I’ve had the longest pseudo-relationships with actually call me. The longer I’ve dated, the more I’ve learned to text less and let them pursue me. It may be archaic and an old-fashioned way to court, but I have a hell of lot less anxiety when I’m not hovering over my phone, wondering if the text I sent was “too much.” And that being said…

4. Don’t worry about being “too” anything.

Too forward? Too sappy? Too flirty? Moving too fast? Too candid? Whatever you are, be that on the first date. If you don’t like that restaurant downtown, it’s a lot more powerful to say, “Oh, really? I didn’t like that place when I went. I prefer this one,” than to chirp up and agree with everything he says.

I was worried for a long time about making myself mesh with my potential romantic partner, and now, I say how I feel — kindly, of course. And I’m not afraid to disagree with anything. And you know what? My conversations are more engaging. My dates go better. I’m more confident and the connection is stronger when it happens because I’m being true to myself.

5. Even if you’re not totally sold on him, it’s worth it to go on a second date.

I used to think that if I didn’t feel that have-to-have-you-gotta-love-you-right-now feeling from the beginning, it was a waste of my time. But the truth of the matter is that after you’ve been on dozens upon dozens of first dates, they all start to feel like interviews.

And just like when you’re job hunting, you have to figure out if the fit is good for you. Sometimes you’re on your A-game, sometimes you’re not. Men could turn into our husbands, but first and foremost, they’re people, and they don’t always have stellar nights.

If a first date went fine and I couldn’t decide if I wanted to see him again, I decided to give it another chance. I’ve found that I know in my gut when I absolutely don’t want to see someone again, but if I’m unsure, it’s worth another hour of my time to figure it out.

6. You’re not obligated to reciprocate feelings.

Especially in a city like New York, where women vastly outnumber men and pickins’ feel slim, it’s easy to fall into the mindset that the dudes have the upper hand. In some ways, they do. They could go out with whomever agrees to go out with them whenever they want to. But so can you.

The biggest thing that used to pique my interest was a guy’s interest in me. OMG, he’s so into me! I have to see him again! This could be something! It took me years to figure out that just because someone likes me doesn’t mean I have to like them in return. That’s my choice, and it’s worth making.

7. Don’t date out of fear.

Am I a little freaked out that I’ve spent the majority of my adulthood alone? Do I wonder where I’ll be in three, five, and seven years? And if all of those visions of a happy marriage and children will work out for me? Totally, every day.

But I have more faith than fear in my heart, and I believe — with every eternal optimistic bone in my body — that being single is better than being in bad/good enough/just-OK relationships or marriages. I don’t want to be on my own forever, and my heart says I won’t, even when my mind begs to differ.

But the driving force to date can’t be to make me less afraid. That makes dates feel panicked and scary, instead of fun and engaging, like they should be. Let those fears come, because they will after a while. But then let them go. Choose hope instead.

8. Never give up on love and never stay home just because you’re over it.

If I could pay $1,000 right now to have my future husband delivered to my door, I wouldn’t think twice about paying for the service. It’s quite unlikely that whomever I marry will march up to my apartment (and it’d be a little creepy if he did), so even when I don’t feel like it, I make an effort to do things I love.

I go out with friends, I go boxing or running, I try a local pub, or I sign up for a class I’m interested in. It’s my way of making sure I’m out there without feeling like it’s too much work.
And though it might not seem like much, it’s a way to remind myself that I’m not giving up. I may not always actively seek out dates, but I’m living my life the best I can and am being open to what comes next.

9. The BIGGEST secret to dating? Living.

There are moments when I call my mom in a straight-up, ridiculous, free-for-all messy, sloppy, childish crying fit and get mad as she tries to coach me to be more positive and hopeful about the dating process. I see my friends taking the next steps in their lives: getting into long-term relationship, getting engaged, saying “I do,” and welcoming children. And I question what I’m doing wrong that I’m not there yet.

Unlike landing a dream job or saving up for something you really want, you can’t work hard enough or be something enough to make your dream partner appear. But what you can do to make dating more enjoyable, to give yourself more patience, to be the best you that you that you can be is to live your life.

Do things that make you happy, take trips that open your mind, talk to people who interest you, be curious about the world around you, be kind to yourself, and learn to love every experience, no matter how trying or seemingly endless.

100 first dates is a lot of dating, but without those men who didn’t work out — who weren’t my match, who didn’t like me in return, who didn’t want something serious, who were just trying to sleep with me, who never called me back — I wouldn’t be who I am today.

I thank them because they’re getting me that much closer to my last first date with someone who was worth all those vodka tonics and noisy bars.