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Is There a Safe Way to Escape the Friend Zone?

So you want to go from buddy to boyfriend. Here’s how to assess the situation—and carefully attempt that tricky transition.

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Q: I want to tell a female friend I have feelings for her. Can I—without killing the friendship?

A: In my opinion, building a friendship first is the best way to start a relationship. There’s something incredibly amazing and sweet about a guy willing to put in that sort of time before making the gradual move from friends to something more. But yeah, there is that one caveat—that bump in the road when you want to make the leap from friends to flame. It's hard getting out of the Friend Zone. So let’s talk for a sec.

First off, you should speak up, yes. But you do not have to lay it all on the line and declare your love. (I cringe just thinking about that.) As Match.com dating expert Whitney Casey says: “One word for that conversation: awkward.” Legit. So instead, work your way into it by following these three steps:

1. Get outside opinions. Seriously. Don’t just say you love her and ask if she’s feeling it, too. While that’s bold, it can very easily backfire. “Rather than having a conversation that has the potential to change the dynamics of the relationship in a negative way, why not bring your her into your regular friend group for either a dinner or daytime activity?” Casey suggests. “Have her interact with some of your other female friends, or even a married couple.” Only ask people whose opinions you really trust: Does she seem into me? Would we make a good couple? So not your jokester buddy who never takes things seriously, or that lady-friend who has had feelings for you in the past.

2. Drop hints. Now, it’s time to escalate. Start making little mentions of how you might feel about her. Pose hypothetical situations, like, “If we were a couple, I would ______” or “If I were to ask you out, I would ______.” Women are pretty intuitive, so gauge her reaction. Here’s another way to say-it-without-saying-it: “Your Hail Mary is this: Ask her to a movie night and watch When Harry Met Sally,” says Casey. “After the movie, ask her if she agrees with Billy Crystal: that men and women can't be friends, that there is always one of them in the relationship who wants to sleep with the other one.” Trust me, she’ll get the hint. If she gives you a shy smile and agrees with Billy, you’re in.

3. Go for it. If the signs point to yes, lay a kiss on her. You’ve probably thought about doing this while you’re drunk, but refrain! There’s nothing remotely clear-cut about that scenario—and ambiguity is the last thing you want. Do it in a relatively private (non-threatening) setting, like on a walk or at her house. She may be totally stoked. She may reject you. But once you get to this point and you've asked every "what if?"...your friendship probably can't survive not trying.

Sigh. My heart is totally swelling in the sappiest way just thinking about it. It’s a risk worth taking—and I’ll be sending positive mental vibes your way as you take the plunge.

About the Hot Girl: Claire Austen is a 20-something freelance writer, sports enthusiast, and polka-dot-lovin’ everygirl trying to bridge the gap between what men know about women—and what women wish men knew. She gives smart, super-honest advice about your biggest dating and relationship conundrums.

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