Q. When it comes to relationships, how do you jump into one from a close friendship? We've known each other for about a year, and over the past couple of months, we've been flirting like crazy, but neither one of us has been able to make the first move. Part of it is that we both know each other so well - especially each other’s baggage - but the other part is we don't want to sabotage such a good friendship if things don't work out. How much do you think things would change if we started dating, and how would I go about dealing with them?
A. Some of the strongest relationships have been born out of friendships, but as you've already identified, there's always the risk of not being able to recapture what once-was if you end up realizing you're better off as friends rather than lovers. So what's one to do? Do you bury your feelings and continue on as friends, knowing deep down inside that you desperately want to jump his bones every time you're together, or do you take a chance and see what might happen? A good way to help you make this decision is to consider the thought of him meeting another woman. If the very thought of this burns you up inside, you need to act fast.
Despite the fact that you tease and flirt, neither one of you has actually declared your attraction towards one another. So before you start thinking too far down the road, the two of you need to get on the same page, and that requires one of you broaching the possibility of actually acting upon some of the things you playfully tease each other about. Since you're the one thinking about it, then go ahead and take the reins. The next time the two of you engage in your usual flirtatious banter, it can be as simple as you upping the stakes by saying, "So, do you really want to?" or, "Why don't we then?" The other alternative is to bring it up in a neutral setting and simply let your attraction be known and see how he reacts.
Entering into a relationship with a friend can get complicated - and he may be all too well aware of this himself - so prepare yourself equally for a positive or negative response. If he doesn't reciprocate, sure, it may sting at first - but if you're good enough friends, you'll eventually be able to resume your friendship. Regardless of the outcome, the important thing is that you let him know the truth, because you'll never know what romantic opportunities are available to you if you don't take chances.