My Boy (reference to the TBS show)

There’s a guy, a fellow doctor, with whom I’ve become good friends through work. From the minute I first met him over this past summer I was attracted to him and for the past 7 months we have spent almost every weekend that we’ve both been in town for together, and some days during the week, along with our core group of 2-3 other friends. What has happened since has been the development of a close friendship while he’s continued to casually date (never seeing more than two or three times because he breaks up with them) women he meets online (and I've casually dated as well). He is concerned about major events in my life and always calls me to see how I am doing when I am away on business trips. None of my other guy friends and I do this – hey, we’ll be having beers in a week. I have dated no one seriously both since we met and since my break-up with Flyboy last June (sad, I know, but I’m scared!) And while I believe there’s a definite mutual chemistry that’s evolved between the two of us, he has never taken the initiative to spend time with me alone.

Yesterday this guy expressed to me in conversation the fact that he’s incredibly insecure, and afraid of pursuing a real relationship because he fears a woman he’s extremely into will ultimately reject him, implying that he toys around with online dating in order to feel like he’s really in the dating game when the truth is he’s not at all secure enough to be. I'm not at all cocky, but as we talked about this stuff, he made eye contact the whole time, blushed, and touched me, all indications that he might be slightly more into me. My question to you readers is – how do I broach this subject, and, more importantly, do I broach it?

From our friendship, I know there are many reasons why we would make a good couple (we have a ton in common both value and personality wise, right down to our deep seated insecurities and history of having been late bloomers in dating). I feel a physical attraction. My rational mind (which has read HJNTIY) tells me if he were into me, he would have made a move by now as he’s a guy and clearly capable of doing so, that I’ve simply been put in that 'just friends' category. The truth is that, on occasion, I’ve become slightly angry at him for not having acted sooner, and probably acted colder than I’ve wanted to towards him, as a result, perhaps driving him away? My less rational (i.e. emotional) mind says this guy and I could be very good for each other, we have great conversations, he eases the stress of my normally taxing workday, I think I do the same for him, and we connect emotionally (and physically, well, in my fantasies, at least).

If you’ve read my past posts that involve fwb, he does NOT know about him - fwb has since left the area, gone overseas, in fact. Also things with my male friend (see December 19th post) who I was seeing over the holidays never sizzled, mostly due to my lack of attraction, so that issue is a non-issue as well…

The more I think about it, the more I just freeze… What’s a girl to do (if anything)? Relationships are hard enough, but potentially putting a friendship on the line is even harder.