Dating Your Friends: Lazy or Romantic?

dating your friendsHow many films or TV shows have you seen where the romantic storylines involved (best) friends hooking up and falling in love?

Popular TV series Friends and How I Met Your Mother based entire seasons on this premise.

As for movies, My Best Friend’s Wedding, Friends with Kids, Friends with Benefits, Made of Honor and Win a Date with Ted Hamilton were the first movies that came to mind.

And while we rooted for some of these friends to hook up, fall in love and live happily ever after, we weren’t that crazy about others because it felt like their love came out of nowhere. Like they were bored, they needed someone, so they turned their attention to the most suitable (or convenient) person around them.

In other cases, even though we liked them as characters somewhat, we weren’t crazy about their timing. For instance, whoever thought ditching a decent person at your wedding was romantic?

And how lazy and inconsiderate do you need to be do realize you’re in love with your best friend right after they announce their engagement?

Yes, you need to be friends with your loved one to make it work in the long run. And there are many great real life stories where friends fall in love and are still happy together. The brother of one of my best friends is just one perfect example.

But should you just start dating your friends “just because”? Of course not. So below are some helpful guidelines to help you decide:

  1. If you’re just going by the statistics and realize everyone else seems to be doing it, it’s not a good enough reason.

At the beginning of season 6 of Friends, Chandler and Monica had decided to move in together, and Ross and Rachel had gotten married by mistake in Vegas when they were drunk. So Joey, being the not-so-smart member of the group, half-jokingly asked their remaining friend Phoebe:

Joey: So Ross and Rachel got married. Chandler and Monica almost got married. You think you and I should hook up?

And that right there shows exactly how not to go about trying to hook up with your friends. Chandler and Monica worked for some reason, and Ross had a massive crush on Rachel before they were really friends.

But when writers threw Joey and Rachel together, we didn’t take them seriously as a couple. And thankfully, it served as a temporary and hilarious storyline.  We didn’t buy it, and neither did they, apparently. They decided to break it off when they couldn’t manage to have sex with each other, on the grounds of having been too great friends for too long.

  1. Don’t get drunk and sleep with your friend to feel better.

OK, so it worked for Monica and Chandler (Friends), but it usually spells disaster in real life. Sure, she got Chandler instead of Joey (which was a coincidence), and things did eventually work out. But is it really a good sign when the first time you found your friend irresistible was after a couple of too many shots?  (How Monica and Chandler got together in London)

  1. Skip the relationship/flirting and just have a baby together because your clocks are ticking, and you don’t want to wait – aka the movie Friends with Kids.  (Trailer, Friends with Kids)

So you’ve hit that certain age where you’re ready for a baby, except you’re single, and the only suitable parent candidate is your best friend. Okay. After giving this a lot of thought, you decide to go for it. There’re a million things that can go wrong with this scenario, but the least you can do is use artificial insemination and not actually sleep with them, right?

Except the movie adds an even bigger conflict to the scenario: the friends make their baby the old fashioned way. It all goes wonderfully until they meet other people, and one of them starts having feelings for the other.

Yes, it’s a typical romantic comedy with its ending, so good for the fictional couple. In real life, even if you reach the same ending, it would be worse as the years gone by wouldn’t be represented in minutes.

  1. If you decide to have fun, unattached, educational sex with a friend, you might want to actually remain unattached. (Trailer, Friends with Benefits)

Friends with Benefits is one very entertaining movie, and in theory, the friendship the two people “ruined” wasn’t that established to begin with. They’d known each other a couple of months, so it wasn’t that big of a risk. But while they were sleeping together, they did remain close friends. Of course, one of them got emotional before the other. Again, it’s the ending we wanted, but things don’t go that smoothly in real life.

5) Don’t realize you have feelings with your best friend just when they announce they’re getting married or involved. (Made of Honor)  (My Best Friend’s Wedding)   (Win a Date with Ted Hamilton)

After you’ve gotten so familiar with someone, it might be hard to notice or come to terms with you have emotional and sexual feelings toward them. It might be convenient not to think about this at all and date other people. After all, what if they don’t feel the same way?

Of course, in defense of Patrick Dempsey’s character in Made of Honor, he did realize he loved his best friend when she went away to Scotland for 6 weeks.

So it might be a good idea to risk getting disappointed instead of waiting for years. A real friend won’t dump you or let you feel weird if they don’t feel the same way. They will do their best to minimize the awkwardness. You owe them the same level of effort.

What’s not cool, however, is to go after your heart right after they’ve promised theirs to other people.


I’m not saying you have control over your feelings. Sometimes you fall for the most unexpected (or in these cases, the most expected) person. I’ve to admit, I risked a friendship because I had a crush on my friend. It all turned out to be fine, just not romantically. I was lucky he was mature enough not to let it affect the friendship at all. But in my defense, I had known him a couple of months, I was completely sober, and he was pretty much what I wanted in a guy.

But ruining a friendship for the sake of temporary escapism and fun is a risk might not be worth taking just because you got lonely, depressed or bored.

How about you? Have you ever dated a friend? How did it work out?


Pinar Tarhan is a freelance writer and blogger for hire. She loves writing about dating, entertainment, writing and career management. You can catch up with her on Twitter, or her blog Addicted to Writing.

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