How to Go From Friends to Lovers

Confession: I don’t like dating much. I prefer when my guy friends seamlessly transition into boyfriend or boyfriend-like tendencies.

Actually, I take part of that back. I like the idea of friends becoming lovers, but there is nothing really “seamless” about the transformation.

Remember the whole When Harry Met Sally adage that tells us men and women can’t be friends because the sex part gets in the way? Well, Billy was right. Sex always gets in the way. Always. And when the sex part gets between two hella good friends, it can go either way: super awkward or super awesome (as nakedness often goes down).

Turning a girl friend into a girlfriend can be bumpy territory, but that’s why I’ve enlisted top Toronto psychologist, Nicole McCance, to walk us through it.

The Approach

Nicole recommends testing the waters at first and asking your gal pal for some relationship advice to see if she bites. “Ask certain questions to feel out if she is interested,” says Nicole. “For example, ask her for relationship advice. ‘What kind of girl do you think would be good for me?’ Start talking more seriously that you are looking for a relationship in general. Be honest and tell her that you would love to meet a girl with her qualities. See what she says. If her response makes it obvious she wants to stay in the friend zone, it won’t feel like rejection because you didn’t ask her directly.”

Also, on a personal note (did I mention I have a lot of experience in this area?), I would go with your gut. If she’s not giving you an obvious sign that she’s interested, then she’s probably not. It sucks, but it’s better to know as soon as possible so you can move forward. If you absolutely must be certain about her feelings, then be direct.

But, as Nicole warns, do not approach your friend when copious amounts of booze have been consumed. Or if you’re dating someone else. She also adds, “Be sure you are ready to get into a relationship, if you do take it to the next level. You have more to lose with this person than another person that you have no history with and will never see again.”

She’s Into It. Now what?

You’re no longer in the Friend Zone. Congratulations! So, what’s next?

“If you are going to become lovers, then start a relationship like you normally would: date her,” Nicole recommends. “The courting period is important and now you can ask more meaningful questions about what she wants for her future, etc.”

I definitely agree with this point. I think often times when friends become lovers, the dating phase is skipped over because you know each other well enough that the “first date” often feels more like the fifteenth. Assumptions are made and important questions aren’t asked because, well, things are blurry. But, if you’re serious about her, and her feelings, then you’ll move slowly.

“The woman feeling that she is being courted is important,” says Nicole. “It’s important that she feels special and that you break your friendship routine and take her out on dates. Ask her the same questions you would if you were on a real date.”Basically, you want to make sure there is an emotional connection between you. There’s a difference between getting along as friends and connecting as lovers. Dating will help with that, while also making it way less intense for the both of you.

What’s So Great About Dating a Friend Anyway?

So many of the very best things! “You already know that you have fun with this person, you know a lot about them and you feel comfortable with them,” Nicole says. “Every good romantic partnership has a solid friendship foundation. If your friendship with her can have sexual chemistry and a deeper emotional connection, it could be a lasting committed relationship.

I mean, what wedding doesn’t have a bride or groom, or both, proclaiming, “I’m so lucky I married my best friend!” It’s what Jason Mraz songs are made of. We all want the comfort and security that a friendship provides us along with a romantic relationship that keeps us hot and bothered. It’s the best of both worlds, right?

But What Are the Pitfalls?

Well, we’re not going to lie to you: you risk losing everything. A girlfriend and a girl friend. “As soon as romantic feelings are involved, your friendship changes. You risk losing your friend if you break up,” Nicole says. “The friendship will never be the same. It’s hard to undo feelings and have it not be awkward right after.” Yep, it’s pretty hard to ever go back from seeing each other’s bathing suit parts and being cool after all the exchanging of feelings and bodily fluids. Also, when it comes to sex with a friend, voicing expectations is pretty important, too.

“If your feelings are involved, let her know before you have sex or as soon as possible afterwards,” Nicole says. “She may think you are just friends with benefits and you risk getting hurt if you say nothing.

Though I haven’t been able to truly be friends with a guy after we bumped uglies, Nicole says it’s possible. “I have seen friendships rekindle,” she says. “It is possible to be friends again, but it can take time.” Fingers crossed!

So Is It Worth Taking the Chance?

It depends on how much you value you place on your friendship with this woman and if you’re willing to risk it all.

“It could be a romance based on a solid friendship,” says Nicole. “The question is: are you willing to risk the friendship? Be aware that your interaction with this person will change now that feelings are involved. As soon as you are in the romantic relationship zone you risk getting hurt. You will find that you may take things more personally and become more defensive because now you care more. You are more vulnerable.” Ahh, vulnerability. It’s a tricky thing. We want all the benefits it reaps, but we don’t want the repercussions from it, either.

From personal experience, I would say: proceed with caution. If your girl friend is someone with whom you can honestly see yourself dating for the long-term, then try it out. But if she’s someone who you’re just curious about (a.k.a you wanna bang), I’d leave her alone and go for the pretty stranger at the bar. Why ruin a perfectly good friendship for one awkward night of sex?

Brianne Hogan is a freelance writer based in Toronto, something of a humorist, and considers herself more Bridget Jones than Samantha Jones. Though she won’t reveal which parts, she will admit to liking emotionally unavailable men and drinking lots of wine.  You can follow her on Twitter  @briannehogan.
Photo courtesy of Roland Selivanoff

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