How to Ask Out a Friend—Without Making It Weird

THE FRIENDS TO lovers trope is a feel-good story everyone from hopeless romantics to love skeptics can get behind (you can’t tell us your heart strings weren’t at least a little tugged at the end of When Harry Met Sally). And thanks to the current boom in romance fiction, with readers over on TikTok sharing their favorite romcom tropes, friends-to-lovers is having a real moment.

Watch it play out on the big screen or in a romance novel, and it looks so easy. Have a crush on a friend and want to ask them out IRL, though? Yikes.

The stakes are a bit higher then asking out a stranger you’ll never see again, or from behind the safety of your iPhone via an app. If this person is someone you see often (especially within the context of a larger friend group), it feels as though there’s a lot riding on that question.

“When you’re trying to ask out a friend you’re looking to fundamentally shift the relationship into a new dynamic,” says Gigi Engle, a certified sex and relationship psychotherapist and resident intimacy expert at dating app, 3Fun. “This comes with a whole host of logistical and emotional complications.”

Here’s how to ask out a friend without making it awkward.

What’s the best way to ask out a friend?

HONESTLY, THE SAME way you’d ask out anyone else. The conversation just might not be as easy.

You might have to be a bit more vulnerable, admitting that you’ve had some type of feelings for a bit and would like to explore them—hence why the stakes feel so much higher. Vulnerability is hard, and having a conversation like this can be scary, but, you never know what might come out of it.

“Honesty is the best policy. Just be open about how you feel,” Engle says. “If they’re a good friend, they’ll be understanding at the very least and if they share your feelings they’ll be happy you felt comfortable enough to be honest with them. Trying to play games isn’t the answer.”

If you’re friends with someone through a larger group, there might a bit more to consider. Friend group dynamics are inherently messy (ever watched Friends?) and this may stir the pot.

“The group just won’t function in the same way as it did before—not necessarily permanently, but for a time, at least,” Engle says. “You also run the risk of your romantic interest being met with some hostility from the larger friend group if they think you’re threatening to upset the delicate ecosystem that is a larger friend network.”

This shouldn’t necessarily stop you. If these people are real friends, they should be open to having honest conversations about this so you can all adjust properly, and clear the air of any bad feelings.

How do you get past the awkward phase if they say no?

WE CAN’T PROMISE a happy ending. Rejections happen, and they’re not a reflection on you as a person.

Sure, it’s going to feel bad for a little. But, “don’t run away from the discomfort,” Engle says. It’s all about staying as honest as possible with your friends as you move through the disappointment.

“Have honest and open conversations with your friend and your wider friend group to ensure everyone is on the same page,” she says. “We have to be willing to accept no with graciousness because not everyone will feel the same way as us.”

Do what you have to do to get over the situation. That might mean a lot of self care, trying new things, and maybe hanging out with some different friends for a bit. You probably desperately want to go back to the way things were—and you can get back there, it just might take a bit of time for you to fully get over the situation.