20 Twentysomethings on What It’s Like to Date in Your 20s

Ronnie Kaufman

Teen Vogue's Twentysomethings Guide is your go-to resource for the more confusing parts of going out on your own.

Trite takes on dating in your 20s aren’t hard to come by. From advice that’s really just 50 ways of saying “put yourself out there” to platitudes about the number of fish in the sea, you’ve probably already heard the greatest hits. Much of that advice — paired with the “designed to be deleted” and “find your person” slogans on dating apps — frames dating as something to get through for one purpose: securing a long-term, monogamous partnership. Ideally, one sanctified by a ceremony that costs as much as a college degree. The truth, though, is that there are just as many ways and reasons to date as there are not to date.

Are your 20s a good time to find the people you’ll connect and grow with the most? Absolutely. But romantic partners are just one version of that. As you move through your 20s, know that there are outcomes that matter a whole lot more than any partnership status does. This includes whether dating has helped you deepen your understanding of yourself and learn new ways to show care in all of your relationships. Has it helped you discover what mettle you’re made of after heartbreak and, just as importantly, have you been able to have some fun along the way?

So, we asked 20 twentysomethings — some single and loving it, others currently partnered — to share their honest insights on those aspects of dating. They told us about the highs and lows of dating in their 20s, the lessons they’ve learned, and what they would tell their teenage selves to expect, to watch out for, and to get excited about.

These responses have been lightly edited and condensed for clarity.

1. Try to take expectations out of dating — including those you put on yourself.

Alessia (she/her), 26: In my early 20s, I felt a lot of the societal pressures to find “the one,” which I had been raised to assume was a man. Dating started as more of a task rather than something I could have fun with and I began most of my encounters with the intention of getting into a relationship. This ultimately took all the fun out of it. However, that changed when I realized I liked women. Dating became more experimental, lighthearted, and fun because it was like making new friends.

Dating at the beginning of my 20s was confusing because I didn’t know what I was looking for and this initially felt scary. However, I learned that knowing what you want comes from discovering what you don’t [want] and experimenting from there. This allowed me to switch my mindset where “not knowing” became exciting as it opened up a world of possibilities.

2. Dating in your 20s may not feel straightforward, but you get to choose what it looks like.

Lucy (she/her), 24: Dating in your 20s is harder than dating in your teens because everyone has their own lives. In your teens, you get to see your crush in geometry class and know exactly what they’re doing this weekend because the big football game is that Friday and everyone you know will be there. In your 20s, everyone works and is busy, so trying to make schedules line up can be the worst. Your dating pool is a lot bigger, but it's hard to figure out where to find the right people. Dating apps can be scary. You don't want to date your coworkers and meeting guys at bars tends to be a recipe for disaster.

You should be excited, though, for the fact that guys actually take you on dates and will court you. You can be way more exclusive with your standards of what you will allow in your life and what you cultivate for yourself. I’ve learned how to really stick to my values and be my own person. Not everyone is meant for you and that's okay.

3. During dates, look for shared life goals and values, not just for someone who’s “on the same page” as you today.

Alissa (she/her), 28: You shouldn't be looking for someone who is “on the same page” as you because a page is only a moment in time. And in your 20s everyone is heading on different trajectories and advancing at different rates. Look for someone who is heading toward the same goals you are. I had some perfectly nice, respectful boyfriends in my early 20s, who may have been on the same page as me at the time, but it didn't and would've never worked out as the years went by because we were heading in different directions at different rates. And, honestly, while those breakups might not have made sense to me at the time, I'm glad they happened because it allowed me to figure out what I want and don’t want in a relationship.

4. Know that even right, rewarding relationships feel hard sometimes.

Rodrigo (he/him), 23: I would tell my teenage self to brace himself [for dating in my 20s]. I feel like everyone has this idea in their head that they’re going to find the right person, and it will be like a fairytale, and everything will be so easy and joyful. That is simply not the case. Love is hard work. Dating is hard work. It takes a lot of dedication, self-reflection, and patience to find the right person. But when you do, love is one of the most euphoric feelings you will ever experience. Being loved, dating the person you chose, and experiencing life with them is one of the most beautiful things about pure and authentic human connection. So, rest assured that all of the shitty dates, shitty guys, and shitty tears will all be worth it.

5. If you ever feel like you’re losing sight of yourself, it’s time to step back from dating.

Keya (she/her), 28: [As a teen] I thought love was going to be like the romantic movies and TV shows I watched. As a result, I started looking for love in the wrong places and dating men who didn’t respect me. In my mid-20s, I fell in love, lost myself with that same person, and after becoming single in my late 20s, learned to love myself and put myself first after my breakup. Currently, my dating life is on pause. I’m open to dating, but I’m more focused on pouring into myself and loving myself first.

I’m now okay waiting until it’s my time to meet my person. My approach has changed: I’m learning to put my needs first, watch out for red flags, and be comfortable in my own skin. It’s okay to be myself.

6. Life doesn’t end when your first love does. Really.

Rachel (she/they), 25: I’ve learned so much about myself from dating in my 20s. I learned that life doesn’t end when your first love does. I became so much stronger from the ending of that relationship. I learned that I'm poly, which has, in turn, taught me about my relationships as well as my relationship with myself.

I learned that queer relationships look really different than straight ones and that's a good thing. I feel so equal with my partner and never question power dynamics the way I always would. I learned that I'm still figuring out my sexuality and probably will be for the rest of my life and that's okay.

I would tell teenage me that it's not weird I didn't have sex until I was 19 and that, in fact, the sex has only gotten better as I've gotten older.

7. Actually, age does matter.

Erin (she/her), 29: If I could go back and give my teenage self some dating advice, the first piece would be: Steer clear of anyone 10 years older than you (or more) while you’re in your early 20s. A 20-year-old should not have enough in common with a 30-year-old to warrant a relationship, full stop.

Also, be prepared to be hurt and to be the one accidentally doing the hurting; You’re young and hurt can happen as we try to understand ourselves.

8. You can be alone without being lonely.

Sam* (she/they), 27: I was so closeted, even to myself, as a teenager. Once I finally left my very confining cishet communities as a twentysomething, it hit me all at once. I was so excited to come out, start dating people other than men, and try dating in ways that felt nontraditional. It's made dating feel so much more fun and easy.

[But I’ve also] learned how to be alone without being lonely. For much of my 20s, I was dating nonstop, with a few short-term relationships. In the last year, I haven't been dating at all and I'm learning how to get self-worth internally. It's a radical change for me. I used to be addicted to the validation and instant gratification of dating apps. I imagine that once I start dating again, I'm going to stay off of them. I find them taxing on my mental health and they don't allow me to connect in the way I'm seeking.

9. Although worthwhile relationships won’t always feel easy, pay attention if you’re often in emotional pain.

Tyler (he/him), 28: I would tell [my teen self] to pay attention to your emotions, particularly pain. Pain is trying to tell you that something is off within yourself or your environment.

I dated the same girl for about three and a half years and it was an emotionally abusive relationship. The breakup of that relationship nearly broke me and I struggled to find self-worth. But because it ended and I’d lost most of my friendships [as a result] of it, it forced me to reach out to people and become more social. About three months after the breakup, I met my best friend, who became my best man at my wedding. I grew to become a better, kinder, and more compassionate person because of the experience and I started dating just for fun rather than to get married.

10. Mixed signals from others will matter less as your own signals get clearer.

Karen (she/her), 29: Dating in my 20s was a rollercoaster of emotions – messy and confusing at times, but also thrilling and full of excitement. It often felt like a series of guessing games, trying to decipher mixed signals and navigate vague communication. However, as I grew more confident, and learned to advocate for my own desires and needs without fear of how my partner would respond, the experience became more empowering and fulfilling.

11. Believe people’s actions over their words, every time.

Abigail (she/her), 29: I wouldn't be the person I am — wouldn’t be as good of a therapist, friend, or partner — without my experiences in my 20s. The worst period of my life was deeply tied to a toxic relationship that eviscerated the best and worst parts of me. Without that dating experience, I couldn't have decided to change everything and learn how to be open enough to date the right people for me. When I was able to concentrate on dating for more or less the first time, I was lucky enough to have had enough therapy to know that when I met the person who made sense for me, I needed to see it through. I eloped one month shy of 29 and I’m grateful for it every day.

12. Slow down, be intentional, and when it comes time to do the hard thing, do it.

Megan (they/them), 29: I don't quite know what my expectations for dating in my 20s were, but they didn't include getting sober followed by a global pandemic. Both of those threw off my “game” a little bit, but what they really did was make me slow down and be more intentional about dating. After being single through my mid-20s, I've been in the longest relationship of my life for the past three years. From dating, I've learned how much of a people pleaser I can be and how to curb that before it goes too far and everyone gets hurt. I've learned that having hard conversations or even fights doesn't have to end a relationship, but not having the hard conversation is a sure way to end it. I've learned that I snore a little bit and that I can't wait for sex in my 30s.

To my teen self, I’d say, “You're queer, so please stop pretending you're not, for the love of god. Stop having crushes on your friends and just kiss a girl. It's not as scary as you think and I promise it'll be worth it to put your real self out there.”

13. In the end, there isn’t a way to protect your heart — and you can hurt or limit yourself trying.

August (he/him), 26: To my teen self, I’d say, “Remember that fear you had of commitment? Remember how you would lead with it and you thought it was charming, like, 'Oh, look at him, he's self-aware?' It's obnoxious, man. If you're not interested in something long-lasting then, hey, keep trying to protect your heart by not being open to longevity. You'll learn after much, much too long that nothing protects your heart, so you might as well try to be open to the future with someone.”

I still get dates the same way I did as a teenager, essentially by getting someone’s number in person, only now I’ve met them at a coffee shop or a show instead of at school. The difference today is in patience. It’s in knowing when a great new person is a friend and not the next coffee date I need to go on or I'll die, in feeling comfortable being single for months at a time and actually knowing the standards I hold for real connection, and in knowing when I'm not in the space to date in a way that is future-oriented.

14. It's a beautiful thing to grow secure within yourself and not date for validation.

Michele (she/her), 26: Dating can be so confusing: What do they want? What do you want? Where is this going? Where do you even want it to go? Do they care more about this than you and does that even matter? I’d tell [younger me] to expect less lows — maybe less highs, too. The good news: Your hormones balanced out, so dating doesn’t feel like emotional whiplash anymore. Dating is so much more fun now. It took too long to realize it, but you’re allowed to be in charge. Who knew? You’re allowed to say, “No,” and you’re allowed to set boundaries and ask for your needs, whether emotional or physical, to be met. It can be deep and lovely or casual and fun. You get to make that choice now.

Every day, I’m thankful to be in my 20s and getting to date how I please. At this moment, I have no desire to be a partner. Younger versions of myself so desperately needed to be loved and validated, but with age, I’m starting to understand that being alone is okay. Not getting a text back feels less likely to change the course of my life now. Nothing really has to matter if you don’t want it to.

15. Don’t try to force it. Things really do tend to happen in their own time.

Halle (she/her), 22: Our 20s are a time when we learn so much about ourselves and overall a time when we are just figuring it out. I would tell my teenage self to not freak out when it comes to dating and just live in the moment rather than searching for someone. The right person will come along when the time is right. And, although I can't speak from experience, I've learned from watching my friends be in relationships that good communication lays the foundation for a healthy, balanced dynamic between you and your partner. This is something that I will look for in a partner, which I only recently realized will come at the right time — and not through forcing it.

16. You can’t hide from your own motives.

Courtney (she/her), 22: I learned that, at the beginning of my dating experience, I didn't fully love myself. Truly loving yourself is really important before you get into any relationship. A lot of times, I have self-sabotaged in relationships just for the sake of having some guy around who didn't really care about me. My approach to dating has changed a lot because I believe at first I was doing it for validation. I carried myself as the chill girl with no boundaries, but was obsessed with the outcome, the “what it could have been.” Now when I date, I ask myself: What is it that I want in someone? Is this person a good fit for me? Do they align with the goals I have? If they don't check my boxes, I learned it's totally okay and to move on to the next.

17. You don’t need to already believe someone is “your person” before dating them. That’s why you’re dating them — to find out.

Natalie (she/her), 29: Coming from an evangelical Christian background, I very much held the view that dating should be reserved only as preparation for marriage. Throughout my 20s, once I was living on my own, I developed my own view of dating. It’s okay to get to know people through the process of dating instead of waiting to date people once you know everything about them and have vetted them as a potential husband or wife.

18. There’s a whole world of dating styles out there. You won’t like all of them, but they’ll all teach you something.

Yasmine (she/her), 25: Dating is different for everybody and it’s definitely not a straight line forward like it may seem in movies or on social media. Just like people are inherently different, so is everyone's dating style. Some people will sweep you off your feet on a first date and some will make you question why you even said yes in the first place. But every date, I think, helps you better understand what you want and need. So don’t be too down on yourself if things don't work out immediately. It’s much better to know what you want, even if it takes a while to find someone than to settle and be unhappy. And definitely be excited about the experiences. Even if it doesn’t work out, at least you tried things you might not have: food, travel, shows. It’ll help you grow as a person.

19. The more you invest in your own well-being, the likelier you are to attract dating partners who will do the same.

Ansley (she/her), 29: I would tell my teen self that dating in your 20s is equal parts fun and harrowing. All the ups and downs, disappointments, excitement, and heartbreak teach you something new and it’s all worth it in the end. The best part of dating in your 20s is that you think it’s about hooking up or finding a partner but, really, it’s more about self-discovery and learning what you want in life. I realized that every guy I dated was actually a mirror image of my own feelings about myself and my self-worth at that time. The more I invested in my own well-being, the more high-quality partners I attracted.

If I had to give my teen self one piece of dating advice, it would be to not trust people too quickly and guard your heart a little bit, not out of fear, but out of how much you value yourself, your time, and your energy. Oh, and never date a stand-up comedian.

20. Don’t try too hard. The best things often happen in unexpected ways.

Ally (she/her), 28: If I could help prepare my teen self for dating in my 20s, I’d say, “Don’t try so hard. There’s a reason you lose interest in a guy just as they gain an interest in you — you don’t like guys. When you finally figure that out, just be yourself. Everything will become so much clearer. You’ll gain respect for yourself and realize that trying too hard (even with girls) doesn’t make for a good relationship. The best ones develop naturally. Even still, heartbreaks are inevitable. Just know that the relationships that don’t last were never meant to. Finding the right person takes time, but you will eventually, and in the most unexpected way. Until then, love yourself and, for heaven’s sake, stop pretending you have a crush on Harry Styles. No one actually believes you anyway.”

*Indicates names have been changed for subjects privacy.

Originally Appeared on Teen Vogue