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Swipe This! Why do I stay friends with my flings on social media?

As you might guess, this isn't in your best self-interest.


Nayomi Reghay


Published Dec 4, 2017   Updated May 22, 2021, 9:12 am CDT

Swipe This!” is an advice column about how to navigate human relationships and connections in an age when we depend so heavily on technology. Have a question? Email [email protected]

. . .

Dear Swipe This!

I recently dated a guy who was everything I wanted on paper. We had a great time on our dates, and we had sex, but shortly after, he told me things had reignited with an old girlfriend. I was disappointed but I took it in stride. I also had a feeling it wasn’t going to last.

Still, I stayed friends with him on social media and now and then I would reach out to say hi. He liked my pictures and posts and I felt like there was some lingering interest. So when I saw he was single again, I waited (I didn’t want to seem too thirsty) to make a move. But when I asked about his new single life, he told me he was already dating someone new, AGAIN!

I couldn’t believe it. Like, how did I miss my window? Or was this just another brush off? Was he ever really into me?

This isn’t the first time I’ve stayed friends with someone I dated briefly. I guess I’ve made a pattern of this, especially since social media makes it so easy to keep up a facade of friendliness. Usually what happens is, we go on a few dates, it fizzles, but I feel like they aren’t a bad person for rejecting me. They obviously have qualities I like. So I try to put my hurt ego aside and strike up a friendship, mostly via social media.

I also have to admit maybe a part of me hopes that friendship might turn into more. My ego says, “Why wouldn’t they like me? I’m great! They just need more time to bask in my amazingness.” Also, I’ve watched a lot of romcoms. Fuck you, John Hughes!

There is also a rational part of me that thinks I’m fixating on this guy in particular because he was hot and I want to prove my worth. But the irrational part of me can’t let it go…and thinks maybe I was meant to marry him?!

Did I ever have a chance with this guy? Is it a mistake to think I can stay friends with the guys I’ve dated? Why do I keep doing this?


Cool Girl Who Can’t Let Go

. . .

Dear Cool Girl Who Can’t Let Go,

First of all, I love me a John Hughes movie, so I feel your pain. I grew up on Sixteen Candles and Pretty in Pink and the myth that girls who are good and patient might suffer through forgotten birthdays and awkward school dances only to one day, eventually, after a long period of feeling invisible, suddenly be noticed by a very special guy. It’s a masochistic fairy tale that I subscribed to for far too long. It’s seductive, it’s fun as hell to watch, and if you apply it to your actual dating life you are signing yourself up for a world of pain.

I do want you to know that pining for people who don’t return our affections is totally human. At one time or another, nearly all of us have wished that someone just out of our reach would want us back. It stings. It sucks. It makes you want to lay on the couch with cookie dough or a glass of wine or, if you’re me, a nice wheel of brie and sink into some of those romcoms that you’re so fond of.

But we can’t sit on the couch forever. We have to make a choice to let go and make room for something new to grow. You cannot cast people in a movie they didn’t audition for, and you cannot connect with the people who are right in front of you if you are forever gazing longingly at someone else.

The trouble is social media gives us every opportunity to keep on gazing. And it gives us the illusion, as you point out, that we can be totally cordial with people who haven’t been all that terrific to us. You say this guy was “hot” and “great on paper,” but he doesn’t strike me as terribly nice or thoughtful. He seems like he was briefly fun and soon became distant and unavailable, which are terrible traits in a committed partner, but perfect traits if you’re looking for someone to cast as your unrequited love.

And please remember that you are the one casting your life. So why are you casting all the men who have disappointed you as your friends? To be fair, I have friends who develop wonderful, cherished friendships with their exes. And if you were writing to ask me if friendship with a former fling was worth pursuing I would tell you there’s no wrong answer. But you aren’t. You’re writing to me because you have a habit of pursuing friendships in hopes of something more. You have somehow developed the belief that if you make yourself nice enough, likable enough, and accommodate another person’s every need, they will somehow fall head over heels for you.

What’s worse, you have social media at your side to help you manufacture crumbs of hope and despair. “Ah, he liked my selfie! This is it, he’s about to realize I’m the one who got away!” “Oh, he didn’t watch my Insta-story? I guess I am actually a piece of unlovable garbage after all!”

When you pursue these false friendships to the degree that you have, I believe you begin to engage in a form of self-harm. One rejection is painful enough. So why set yourself up to be rejected over and over again?

Though cliché, let’s actually consider this question: What do you gain by holding onto these connections? Are you perhaps trying to breeze past the actual sting of rejection and head straight into friendship in the hopes that you won’t have to feel? Or are you dodging the possibility of a real connection by pursuing people who are terminally unavailable to you? Is it safer to engage with people who will never meet your needs than it is to connect with someone who might actually get close to your very tender heart?

If I had to guess, I would say holding onto these ex-flings is a form of emotional hoarding. I remember when I first read The Life-Changing Magic of Tidying Up. I couldn’t believe it. I had a hoarding problem. But instead of hoarding clothes and knick-knacks, I was hoarding dick.

For years, I reused and recycled old connections that did not suit me. And just as Marie Kondo explains that hoarding possessions is rooted in our instinctive belief that we need to do so to survive, I was operating on the belief that holding onto these dicks—possessed by men who couldn’t give me the connection I really wanted—would somehow keep me safe. I took an honest look at her advice (which is to only retain items in your life that bring you joy) and came to the conclusion that if I really wanted to change my love life, I was going to have to discard all this lackluster dick—which was bringing me plenty of feelings but none of which resembled joy.

It wasn’t easy. My dating life did not magically transform itself overnight. And there were times when I was tempted to run back to the trash pile and take comfort in one discarded dick or another. But over time, I truly committed to discarding the dick that did not bring me joy and something happened: I opened up to the loneliness inside of me. I befriended it. Bit by bit, I found that I was kinder to myself. And soon, I realized that the dick I’d been hoarding wasn’t what I needed at all. I had so much more room in my life for joy, that when I did connect with new people, it wasn’t from a place of lacking or wanting for love. It was from a place of wanting to share my joy.

You seem like a very self-aware, intelligent, and charming individual. You also seem alarmingly kind. You deserve happiness, love, and a connection that lasts far longer than the final minutes of a John Hughes film. And I believe you can have it. But first, my dear, you’ve got to discard all the dick you’ve been hoarding.

I can’t promise you it will be easy. I imagine the feelings you are suppressing when you tell yourself, “It’s OK that he didn’t like me, we can be friends!” may come to the surface. Perhaps you will feel angry or hurt. Maybe you will tap into your fear that there will never be enough love to go around. But if you can walk through this fear, if you can clear out your own sacred space for love, I promise you that very soon you will get back to your joy.

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*First Published: Dec 4, 2017, 6:30 am CST