How to make him Harry to your Sally

Sometimes, love surprises you. One minute you’re punching him on the shoulder like he’s your kid brother, and the next thing you know you’re suddenly dying to lunge across a table, grab him by the lapels and plant a clear message on his slightly chapped lips. But when he’s a longtime friend – possibly someone who has counseled you through your countless breakups and already seen you in your least sexy pajamas at the cottage – it can make things a little more complicated. So how do you make him Harry to your Sally?

Relationship advisor and therapist Dr. Terri Orbuch says that it’s not uncommon for a woman to start to feel some warm fuzzies for a man who already makes her comfortable. “Women generally need emotional closeness to feel romantic or sexual attraction,” she says. “Women spend time, disclose personal intimate details and information, share common interests and activities, and laugh and have fun with good friends. All of these activities bond women to their friends and intimacy develops. This intimacy and emotional closeness then may lead women to feel and desire romantic or sexual attraction to a male friend.”

But making a move – even under the best of circumstances – can be a tricky proposition. What if he has a girlfriend? What if he uses some lame excuse, like that he has to go clean out his email Inbox? (Note: that actually happened to me.) The stakes of possible rejection are even higher when you’ve already developed an sizeable attachment to someone. Plus, you’re dealing with a prospective suitor who already knows you well and has ideally embraced all of your quirks; that means that when they reject you, they reject the real you – which is serious ouch potential.

Orbuch adds a few other items to the list of possible difficulties: the rules for a friendship can be different from the rules for love – including greater exclusivity, greater and more frequent obligations – and it’s tough to predict how your relationship will fare the transition; you’ll have to deal with reactions from mutual friends, who might not share your perspective or encourage any upset to the existing friendship balance; and you’ll have to ask yourself whether potential romance is worth risking an actual friendship. What if he’s a terrible kisser?

“Before you do anything or let your good friend know, I think you need to carefully consider the advantages and disadvantages of being honest with your good friend about your romantic/sexual desires,” says Orbuch. But if you’re really feeling it, and if you can’t sit next to him without feeling a volt of electricity shoot through your entire body, you’re probably not going to listen to reason.

So how do you actually go about making this happen? Before you go blurting out everything over your fifth Mojito, consider a little strategy. Orbuch recommends looking before you lunge, and exploring the signals your friend is sending.

• Does he take opportunities to linger at the end of the evening to create a situation where it’s just the two of you?
• Is your friend already in a relationship that could seriously compromise his ability to reciprocate? (And, if so, are you confident that you can handle his current girlfriend in a physical altercation?) · Do you really want to date him in particular, or are you just kind of lonely and bored?
• Once the novelty of being newly sexually involved wears off, will you actually be a good long-term match? Are you even looking for a long-term relationship, and have you considered the possible consequences of a fling?
• Have you run your plan past a trusted mutual friend, who might be able to offer some insight into the situation and the best way to proceed?
• And, finally, does the object of your affections give you any reason to believe that your relationship is special and distinct from his relationships with his other friends?

And now, the good news: studies apparently show that men are much more likely to “romanticize” friendships with women, and women underestimate how much their male friends would like to be romantic or sexual with them. So give it some thought and then get out there, tiger. And if that doesn’t work, you’ve probably got some other cute friends