Dating Guys in Their Twenties is an Unpaid Internship: Lessons from Dozens of First Dates

Dating Guys in their Twenties is an Unpaid Internship

Lessons from Dozens of First Dates


Man oh man. (No pun intended.)

I know the title is purposely comical, but this is a serious topic.

I am not a dating expert. I’m not a therapist or a professor of communication (though I did learn from one of the best). I’ve just gone on a lot of mediocre dates. These are my experiences and those of my friends. These are my opinions. I’d like to share, because it’s through storytelling with other women that I’ve felt less alone in my journey toward healthy, thriving relationships of all kinds.


Dating is downright messy. It’s hard not to hurt or be hurt, and still we do it. For those of us who want to do it with intention and care, it can be overwhelming. I’m a heterosexual woman in her mid-twenties, and though my friends and I have had varied experiences in how we go about dating, the kinds of people we date, and where we date, we have come to startlingly similar conclusions about lessons learned in the process.

I am not crazy, I assure you (that sounds convincing, right?). In my case, going on lots of first dates is indicative of pickiness and relative certainty in my values; I have friends with similar experiences. I’ve always struggled to find boys (men) my age who mirror my maturity and interests. It’s hard for me to write that, because it sounds vain. But I’d like to offer uncomfortable honesty. For whatever reason (ahem, socialization), the behavior of young men in the dating world leaves a lot of us disappointed and confused. I know this isn’t exclusive to men; women in their twenties are equally hurtful and sloppy, and plenty of fantastic men out there are truly doing their best. Regardless of gender or sexuality, we all mature with age. We get wiser, more considerate, more self-assured. Hopefully.

I’d like to think that the lessons I’ve learned in going on an exhausting amount of dates can help more than just women dating men in their twenties. However, I’m willing to bet many of these will hit home especially for them.

Technology really can’t replace face-to-face interactions. Really.

No matter how much time we spend texting someone, sending memes, or sharing playlists, we truly need to meet someone face to face to know if chemistry and compatibility are there. In cases of online dating, I’ve been utterly disappointed or pleasantly shocked at how someone behaves in person after making assumptions based on mediated communication. The way someone speaks, how they are in their body, how they treat the waitress–all of these are vital indicators of attraction. When it comes to going on a date with someone you’ve never met (i.e. setups by mutual friends, online dating, etc.), keep your expectations low but your standards high.

We can do better than ghosting.

This is a hot topic these days, and it’s not conclusively defined. We each draw a different line to indicate the point in a relationship at which you owe the person you’re seeing an explanation if you no longer want to see him or her.  Dropping off the grid until someone gets the hint and leaves you alone is, to put it simply, immature. It’s hurtful. It’s lazy. It’s confusing. It’s all the things we don’t strive to be in our interactions with other humans. Honesty is a practice–it’s not something we can simply “be.” I am not honest unless I’m practicing honesty, and I’m still learning in this department. Navigating the line between pernicious, unfiltered honesty and kind-hearted candor is murky, but it’s a line I challenge us to approach. With care. It’s not often we hear, “Ugh, I wish he/she/they had been dishonest with me!” If someone communicates with you respectfully, reciprocate. It’s probably going to be uncomfortable. You might squirm. But this feels far better than the alternative. I know from experience.

Knowing what you want and need is important, but don’t neglect to examine what you’re ready to give.

Many of us young whippersnappers agree that dating in our twenties can often feel like a winding road on which we learn, through lessons easy and hard, what we want and need from a partner. What am I surprisingly attracted to? What is a total deal-breaker? What seems fun for six dates but then becomes something unsustainable? We figure this out. But many of us neglect to dig deep and examine what we are willing to give a partner. How can I show up for someone? What are my hurtful tendencies? What steps am I willing to take to identify what my partner needs...and am I going to fulfill those needs within my own healthy boundaries? Journaling helps. Talking openly and honestly with friends helps. Time helps. I’ve been burned by men who think they know what they want but who brought me into their lives without honestly scrutinizing what they’re ready to give. It’s through those experiences that I’ve learned to introduce more selflessness into my own ideas about partnership and love–I’m more careful about who I choose to let in and the commitments I can make in good conscience.  

Navigating social media and dating: I don’t think any of us really know what we’re doing.

Throw social media into this messy mix and we’re looking at a spider-man-worthy web of dynamics to navigate. When my grandparents ruled the dating scene, they would have asked each other out in person, perhaps talked on the phone, and, if they broke up, possibly never saw or heard from the other again. In today’s dating world, we Instagram-stalk someone, we see what they’re doing even when we’re not together, we send messages in multiple spheres, and–the worst part–we have to decide how to proceed when we part ways...

“So...how long do I wait before I block him? He’s seeing someone else. I think. Based on his posts, he is. Ugh, why do I know this? I hate that I can so easily know this. It makes it harder to move on. How do I deal with my tendency to check in on what he’s doing?”

“So...I was seeing this guy, but then he treated me horribly and we stopped seeing each other. I unfollowed him, but he still follows me and watches all my stories. It bothers me sometimes, because if you’re not going to be in my life, maybe you shouldn’t get to see what I’m doing. But I can’t bring myself to block him, because I don’t want to burn bridges. What do I do?”

“So...do you think it’s okay to like my ex’s posts even though we broke up? I mean, we parted on good terms, and we were together for a long time, but is a break-up supposed to be a break-up in every way?”

None of us know how to best figure this out. It isn’t something we’ve ever had to maneuver before this decade. Here’s a rule of thumb that’s worked for me: treat someone on social media the way I would treat them if they were standing right in front of me. If you’re not in my real life, maybe you shouldn’t be in my social media life. Each of us might feel differently about this with different people. Trust your gut. Practice discipline.

Don’t forget to be safe. Look out for each other.

This is for everyone. We’re not invincible, and there are ill-intentioned people out there. Check on your friends. Be the person who makes sure friends get where they’re going and make it back home safely. Don’t feel paranoid. Feel prepared, realistic, and smart. Be shameless in your possession of pepper-spray if that’s what makes you feel safe. I hope to one day live in a world in which this isn’t a common necessity.

Don’t compromise your values or standards, but recognize room for growth and maturity.

It’s easy to become jaded, distrusting, and judgmental. I actively work to resist this, and my friends remind me that it’s okay to trust and it’s okay to not expect perfection (“perfection”). I’ll likely meet someone who has room to grow, because we are all HUMAN. I have growing to do, too. The sweet spot is finding a partner who shares core values and expectations, but it’s likely I’ll challenge him in new ways. The right people will meet those challenges and offer their own in return. Recognize someone who shows eagerness to learn, to be kind, to put in the work. Reciprocate.

Boys still think speaking French is the most charming thing ever. This is one cliché that is alive and well.

I know most people aren’t fluent in French, but I had to throw this in. Lesson #7 taught me that, as ridiculously cliché as it may be, if you whisper French to an American boy, he will do what you want. Leverage it, friends.



We each live our own individual dating experiences. It’s hard to put yourself in a vulnerable light, and the fact that we do it again and again points to the innate human need for connection and belonging. I’m trying to be kind and self-aware in this pursuit, but I have learning to do. As with most things in life, I will do the best that I can for as long as I can.