Donate to the Transgender Law Center

11 Real Boys Give Themselves Dating Advice

If you could talk to your younger self about dating, what would you say?

February 12, 2015

It's almost a sick joke that holiday tradition has love and dating on our minds in mid-February. Cuffing season is past us, but the warm thrill of Spring feels eons away. It's a somber time, ripe for reflection. So, we asked a bunch of smart dudes we know—gay and straight, single and taken—to tell us what they've learned about love over the years.

1. Just go for it

Adrian Carter / 28 / Status: "It's getting better"

Adrian: Be confident and be yourself. The worst thing a woman can tell you is "no." Be respectful in your approach and be honest. Women tell me this all the time, so there must be some truth to it.

Follow Adrian on Twitter

1. Just go for it
Adrian Carter / 28 / Status: "It's getting better"
3. Know when to shut up

Colin Stokes / 24 / Status: in a relationship

Colin: Know when to stop talking to someone. I never send more than two messages to someone if I don't hear back. At best, you'll look desperate. At worst, you'll look like a creep. At medium, you'll look very desperate and a little creepy. You're probably going to make the same mistakes multiple times. At least while you're young. You shouldn't hate yourself for making them.

Follow Colin on Twitter

3. Know when to shut up
Colin Stokes / 24 / Status: in a relationship
5. Sometimes getting dumped is better

David Shapiro / 26 / Status: in a relationship

David: Getting dumped is actually much better, despite pop culture's presentation of the "dumper" as the winner and the person dumped as the rejected loser. When I've broken up with someone in the past, it takes less than a week before I start thinking I've made a huge mistake that will be irrevocable if too much time passes and they meet someone else. And so then, most of the time, I beg them to get back together but all the things that made me want to break up with them in the first place are still there, so I'm right back where I started: in a relationship with someone who I want to break up with. But when I've been dumped, counterintuitively, I guess, I wind up much happier knowing that getting back together with them isn't even an option.

Follow David on Twitter

5. Sometimes getting dumped is better
David Shapiro / 26 / Status: in a relationship
7. Love and friendship aren't that different

Jun Harada / 27 / Status: single

Jun: I wish someone had talked me through the nuances of what it means to treat women as equals when dating them. I grew up in Hawaii with two brothers in a pretty jock-centric culture. Making friends with girls was no problem growing up, however transitioning those skills to dating always was muddied by the macho culture of the tropics. It never occurred to me to look at my significant other as a friend and partner—just like my closest friends, and that dating was simply the same as courting a friend.

Follow Jun on Twitter

7. Love and friendship aren't that different
Jun Harada / 27 / Status: single
9. Tell them when it's not working

Tourist / 27 / Status: single

Tourist: You have to be honest. I don't mean honest as in not lying, but if something upsets you you can't bottle it up. I used to be very guilty of that. When someone upsets you, you have to let them know, and you have to figure out why they upset you. And part of that honesty is not kidding yourself. If it's not right, that's unfortunate but you're better off going you're separate ways. Ultimately, if you care about someone but you're not supposed to be with them, the best thing for them is not to be with them. That's one of the most difficult things to accept in life.

Follow Tourist on Twitter

9. Tell them when it's not working
Tourist / 27 / Status: single
11. When it's over, it's over

Eli Schmitt / 26 / Status: in an open relationship

via Sei Ratifa/Getty Images

Eli: I think a lot about the phrase "Burn The Raft," which I might actually be appropriating from Buddhist philosophy. When I say it, I mean: let something go once it has done its job. I have gotten into lots of relationships at certain points in my life because of context—like, it made sense to date a gallery person when I wanted to do art stuff; it made sense to date a depressive stoner when I was depressed and wanted to watch TV a lot. But sometimes things change. I think it's okay to grow out of things so that you can keep growing. I think being able to gracefully end relationships is one of the great skills a person can have. The important thing, especially when you are under 30, is knowing when to burn the raft and start swimming.

Follow Eli on Twitter

11. When it's over, it's over
Eli Schmitt / 26 / Status: in an open relationship
Posted:
11 Real Boys Give Themselves Dating Advice