I went on 10k hours of dates in my 20s—and here are the 10 lessons I learned
As a hopeless romantic who was raised on rom-coms, Julia Roberts and Kate Hudson’s film roles convinced me that the only time I could find love was in my 20s. It didn’t matter if I had a high-powered job, how fabulous my best friend was, or how beautiful (and surprisingly spacious) my New York City apartment looked, I believed I had a window from 20 to 29 years old to go on dates to find The One.
Since I’m a bit of an overachiever, I approached dating the same way I approached anything in my life: with full force (and maybe a little too much enthusiasm). I went up to cute guys at bars when I was out with friends, only to discover they were taken or not into women. I’d let my friends set me up on blind dates and went on two reality dating shows. I even had not one, but two matchmakers try to make me a match, and still, nothing happened. So I tried the next best thing to find true romance: dating apps.
I spent a good chunk of my 20s swiping on almost all of the dating apps that were available, from Tinder to Bumble to Raya to JSwipe (aka Jewish Tinder). But nothing came of it. At first, I thought the apps were the problem, but I never thought that maybe my approach to dating and the guys I was giving my time to were the issues.
Don’t get me wrong. I went on a few good dates. I met people who I’m still friends with today. But while some matches and I would date for a couple of weeks or months, like clockwork, I’d realize later on that we weren’t compatible and I would fire up the apps again.
And then I started to do the math. I was always either swiping, dating, or in a situation-ship or short-term relationship. I went on more dates than the average person, whether it was for coffee, drinks, dinner, or brunch. Sometimes, I would even go on two dates in one day.
At one point, my friends would often make fun of me, because it would seem I would go on a date a day. Over the years, I have easily been on 10 thousand hours worth of dates in my 20s. And according to Malcolm Gladwell, this would make me an expert…a dating expert.
I ended my 20s thinking I had found my person at 29 years old. I uprooted my life, gave up on my hopes and dreams in Los Angeles to support his hopes and dreams in New York, only to find myself even more alone in this relationship than I ever felt when I was single. So we broke up, and I eventually moved back home to L.A. and re-downloaded all those dating apps again.
Apparently, this dating in your 20s fiasco is common, as Ashley Hesseltine and Rayna Greenberg, hosts of the sex and relationship podcast Girls Gotta Eat, tells HelloGiggles, “Dating in your twenties is a wild ride…it’s typically a mixed bag of falling for the wrong guys, maybe finding the right one, [engaging in] drunken hookups, figuring yourself out sexually, sending nudes you’ll regret later, and (hopefully) collecting enough information that you can detect a f*ckboy from a mile away. When you hit your thirties, you’re more empowered, [you] know what you want, and don’t have time for the bullsh*t (because let’s be honest, there’s always gonna be bullsh*t).”
But at 31 years old, I finally realized that rom-coms are B.S.
The truth is, you don’t need to find The One in your 20s or 30s (or by any age really!). I finally felt whole, and I didn’t need another half. If I was going to get into another relationship, it should be with someone who feels whole as well. Once I started dating with this mentality, I went on three dates in three days with an incredible guy, who is now my boyfriend.
Lucky for you, you don’t have to go on 10 thousand hours’ worth of dates to make dating work for you. To help, I provided cliff notes on what I learned from dating in my 20s and the lessons I finally started listening to in my 30s—which I wholeheartedly believe is what led me to the healthy and happy relationship I have today.
10 dating tips I learned while I dated in my 20s
1. Every relationship has an obstacle.
Every relationship I’ve ever been involved in has faced an obstacle of sorts. And if you’re currently dealing with something similar with your partner, it’s up to the both of you to decide if you can either make it work or let the obstacle win.
The most common dating obstacle you may experience in your twenties is distance. Long-distance relationships involve a lot of effort, so if you’re going to try it, it’s up to you to decide if that commute (whether it’s a plane ride or a car ride) is worth it. The best way to decide is to make sure you and your partner are on the same page and putting in the same amount of effort to make time for one another. Otherwise, in my opinion, it’s not going to work.
2. Don’t ignore the red flags.
This advice seems obvious, no? Sure, I was aware of the red flags in my twenties, but instead of dumping my significant others, I became a master of making up excuses for them and their behaviors. I would often say, “Oh, he’s not ignoring me, he’s just teaching me independence.”
In my 30s, I finally noticed that red flags would appear on the first date. For example, I went on a first date with a divorcee and found out before we sipped our coffee that his divorce wasn’t finalized. Or there was one time I learned over beers that this comedian actually didn’t live in L.A. He really lived in Arizona with his ex-girlfriend and their dog (that’s like three red flags).
It’s up to you if you want to try to make the relationship work or not. But while I spent a lot of my 20s trying to ignore red flags, I’ve spent my 30s seeing them for what they are: dealbreakers.
Instead of making up excuses or trying to fix these possible red flags, ask yourself if you can accept these dealbreakers. For instance, if your date confesses they still live with their ex, ask yourself if you really feel comfortable with that situation. Can you confidently date someone whose ex is still physically in the picture? If you honestly can, then go for it. If this makes your stomach turn, then end the relationship before your feelings get even more involved.
3. You can’t make someone like or love you.
As an only child, this was hard for me to accept. Not everyone will like or love you—and that’s okay. Sometimes, there’s no deeper meaning or excuse as to why someone ghosted or didn’t text you back. It might be hard to hear this right now, but when someone likes you, it’s so obvious. It’s when they’re not into you that you become confused. And honestly, who has time for that? Not you, that’s who.
4. Having a type can also mean having a pattern you need to break.
My best friend Joye, who has met most of the guys I’ve dated, used to joke with me by saying, “Gabs, I swear, all of your boyfriends are the same person, just with a different name.” And she was so right. I kept dating textbook narcissists with a slight Patrick Bateman vibe. All of those relationships ended the same way: me heartbroken when I discovered that I would never be a priority to my knight in shining Underarmor. It wasn’t until I finally broke up with my go-to type that I met a wonderful guy.
If you find yourself dating the same type of person over and over again (or maybe your friends call you out on it), it might be time to take a pause with dating and focus on yourself. Hone in on what you want and do not want in a partner and relationship. Instead, stick to your standards before giving someone who’s undeserving the time of day again.
5. Trust your gut. If you think something is off, it probably is.
Let’s get one thing straight: You don’t wake up in the middle of the night in a panic wondering why your partner didn’t text you back when you’re in a healthy relationship. Period. Every time I felt something was off when I was in a relationship, I was right. Like the one time I started to get panic attacks when I was dating my ex because deep down, I felt something was off. While I never found out if he did anything wrong, the panic attacks did go away the second we broke up.
Ultimately, your partner should make your life easier, not more difficult. If you feel like you’re always walking on eggshells with your S.O., that’s probably a sign that you should get out of the relationship ASAP.
6. Your S.O. shouldn’t make you cry.
I used to think it was normal for my exes to make me cry, which is so wrong. Remember that saying, “No guy is worth your tears, and the one who is will never make you cry?” Turns out it’s true.
However, I didn’t fully realize this until I got into a relationship with my current boyfriend, who is always supportive. If I ever cry about something that’s stressing me out, he rubs my back and tries to help me solve my problem. This is the complete opposite of when my ex would tell me that I was being dramatic, every time I would cry over something he said that was insensitive. He would never console me because he didn’t want to “encourage” my crying. But that’s not a healthy relationship. A partner helps you solve your stresses and problems instead of being the cause of them—or making them worse.
7. The minute you realize you’re in a toxic relationship—get out.
Valentine’s Day is coming up, and you might not want to be alone for Single Awareness Day. But if you don’t break-up now, I promise you there will be another event around the corner where you don’t want to be alone. Like your best friend’s wedding, your birthday, your partner’s birthday, and before you know it, it will be cuffing season all over again. Stop it.
If you’re in a toxic relationship, get out now. Yes, breaking up always sucks, but it gets harder the longer you prolong it. So do it now before your lives get more intertwined.
8. The person you keep going back to is not The One.
For eight years, I’d been on and off with this particular ex. While I kept flirting with the idea of us being in each other lives because of the infatuation I had with Carrie’s and Mr. Big’s fictitious relationship, I realized that my ex was actually better as a friend than a boyfriend. When we dated, he’d let me down or not text me back. But when we were friends, he would always be there for me, willing to help me whenever he could.
Eventually, we stopped hooking up. We were never on the same page as lovers, but we could show up for each other as friends. But at the end of the day, this relationship helped me realize what I did and did not want in a partner—and I think you can do the same. Just be honest with yourself and try your best to objectively look at your relationship. Don’t wait and hope that one day it will all work out, especially if it did with your favorite TV show couple. Accept your situation and relationship for what it is instead of wishing for what it isn’t.
9. Never try to turn a booty call into a boyfriend.
In order to be in a healthy and successful relationship, you and your partner must be on the same page about things. However, don’t force a booty call to become something more, especially if that person doesn’t want to see you when it’s light out like a vampire. Don’t take your booty call to brunch, trust me. They might disintegrate. But all joking aside, booty calls can be great as long as you’re both on the same page and can accept the situation for what it is.
10. Dating in your 30s is actually a lot of fun.
Whoever ingrained in our heads that our 20s was the only time to settle down is seriously deranged. I was such an awkward mess in my 20s, unsure of who I was and what I wanted. Now in my 30s, I’m confident, secure and know what I want. I got here by journaling, making a lot of mistakes, learning from them, getting good at being alone, taking time to work on myself, and reading books. I realized that if I wanted a boyfriend, it would simply be a perk—And that’s when I met my person.
I met my boyfriend at a time in my life where I wasn’t looking for anyone. I didn’t want anyone, especially a relationship, to validate my worth or to make my life full. And even though I found my partner now, the relationship doesn’t define me or my life. But it took a lot of work to get here. The lessons I learned from my 10k hours of dates helped me identify what I want for my life in or out of a relationship, and now, I’m present, calm, and can communicate with my S.O. to make sure that we’re on the same page about things. And for the first time in my life, I really feel like I have found The One.
Hopefully, these tips were helpful and will save you time with dating. Dating can be so much fun as long as you enjoy it. So have fun and be safe out there! But if you want more tips, check out my book, Twenty Guys You Date In Your Twenties. You won’t regret it.
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