I should spend less time reading gossip blogs and more time writing advice

Dear Victoria Blunt,

There is a woman that I've known for years who has become one of my closer female confidants. While we have hooked up a few times at the onset of our relationship, my initial wishes to actually date her were generally dismissed, but it didn't matter to me as I valued our friendship and had other women in my life to date seriously. At one point I even thought that dating her would be a bad idea considering some qualities that I am not terribly fond of. During our time as friends, we've certainly shared stories of our past relationships, and I've even hooked her up with some of my friends. So the other day when we were hanging out, she kept making comments on how the men in her life should be more like me, how we have such a great relationship, etc. And she clearly gave me the vibe that she would be open for me to try and date her.

But should I? Do I potentially ruin a good friendship to engage in a relationship that I might have wanted years ago but am unsure of now? I normally have a "no dating friends" policy just for this reason. Also, I should add that I'm dating two other women, so I would probably have to get rid of them.

Sincerely,

Troy Dyer

Dear Troy,

I saw a patient the other day - an older, homeless gentleman- who told me that a woman 20 years his junior has been checking him out at Walgreens for the past few weeks. When I asked him how he knew that she was checking him out (and he is rarely one to make such assumptions), he answered that 'you just know', and that she often went to the areas of the store he occupied at any given time. Now I am not sure as to the size of his local Walgreens, but in hearing this, it was hard to quell my doubts as to whether he was stating facts.

I'm not telling you this story because I don't believe your long-time confidante wants to date you - I am just pointing out that we don't really know these things until someone (rather bluntly) says so. It's not rare for me to tell a close male friend that more men should be like him and that we have a great relationship (after all, being amazingly awesome is a requisite for being my friend). That being said, let's take this at face value and proceed.

It sounds like you're not entirely sure whether you would want to date your friend, never mind knowing what you should do in order to start dating her. I wish you were here right now Troy (granted that yr not creepy in any way), because then, together, we could make a nice, old-fashioned Pros and Cons list. (My favorite!) As it is, yr gonna have to DIY. What makes this woman someone who could be more than just a friend? What was it about her that made you initially want to date her? What is it about her that made you think dating her would be a bad idea? How did you feel when you arranged for her to have a go with some of your friends? I think you want to figure this stuff out before you go any further, because if you decide she is someone you don't want to date, then yr going to have to dig in yr heels and spend some time on operation: save friendship. But that's prolly an issue for another time.

So let's say you decide she is in fact someone you can see holding hands with and smooching at the movies. (I don't know why dating reminds me of the 1950s or 8th grade.) What to do next? Because this woman kept things at a safe, vague distance, it would seem that yr going to have to be the one to take some initiative. So do what I always do when I'm nervous with someone I like: get drunk. Not grossly, embarrassingly sloshed, but a nice pleasant drunk where the two of you could end up making out on a couch without anyone feeling their heart pounding out of their ears. Ask her out to a dive or a lounge or yr couch, and have a few. (If yr in AA or don't drink, then just enjoy that feeling where yr heart is pounding out of yr ears. Whee!) And flirt and be charming and be funny and wear a snappy outfit. Then approach the subject jokingly. Tell her about the last few people you've dated, and why it's not going so great. Say that you wonder why the two of you never happened. When you say this, ACT CONFIDENT. If you pretend it's not awkward, chances are it won't get awkward. Maybe even wink, if she has a good enough sense of humor. But make her stick to the question.

And that's it my friend. She has to take it from there. Good luck!