Transitioning from friends to…

With the opening of Friends With Benefits, it seemed only fitting to answer this question from a reader via Formspring:

How do you transition from friendship to more than that ;)? I’m friends with this boy, and I don’t know how to try and change the vibe because I'd like to be more than friends. Any tips?

Based on how you phrased the question, I'm assuming that you're interested in dating your friend, rather than just something physical. Have you thought about:

  • How much you rely on this guy as a friend?
  • If you lost the friendship completely or it became awkward to be around him, is that worth the risk of trying to transition to more than friends?
  • What’s the best possible outcome in the short or long term? What’s the worst?

There’s no right or wrong answer to those questions, but you need to be prepared as best as you can for all possible options. Is the chance to be with this guy worth the risk of losing him in your life completely?

If the benefits outweigh the risks or it’s becoming difficult to hide your feelings, then think about what he’s said about relationships and figure out how you can change up your normal routine. Some ideas and questions to consider:

1. Is he open to being in a relationship right now? Does he talk to you about other girls or what he is looking for? Is he hung up on an ex? Has it always been just platonic between you two or was there ever any flirtation?

Answering those questions might help you figure out how best to proceed. If he’s still getting over an ex-girlfriend, I might wait to broach the subject. If there was a time when he was flirtatious with you, then I might be more inclined to let him know how you feel.

2. How do you two normally interact? Try to change your routine in a manner that makes it more conducive for the relationship to naturally evolve into something as more than friends.

If you’re used to just working out together or watching DVDs, what if you suggest getting dinner one evening at a quiet restaurant? If you typically socialize with friends at a bar or lounge, what if you offer to cook for him at your place?

If you two interact one or twice in a different mode, does he seem more inclined to go down the dating path? If so, then I might wait to say something for a little bit. If not, then it might be worth proceeding to #3 and actually saying something to him.

3.Talk to him. It’s not always easy to share your feelings with someone, but you’ll never know how he feels unless you do so. On an evening when you aren’t drunk, rushed or around other people, tell him in your own words:

Your friendship is really important to me. But, lately, I’ve started to wonder what it would be like to be more than friends. Have you ever thought about that, too?

Think about how you’ll respond if he says “yes” or “no.” Can you still be friends with him if he doesn’t want to date you? If he’s interested in being more than friends with you, what do you hope for next? If he seems completely caught off guard, let him know that you can talk about this another time because it's not urgent. (It might feel pressing at the time, but it really isn't.) Likewise, if the conversation becomes awkward, you can let him know that you don't need to figure this all out at once and then change the topic. If the guy is interested in more, he'll make a move or bring it up at a later time.

Regardless of the outcome, be proud of yourself for being honest and going after what you want!

Thanks for the great question and let me know how it goes! xoxo

So, readers, did I miss anything?

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