I have a friend, Yvonne, that I’ve known for about a year. Yvonne is a great person, but people she can sometimes dismiss her as being rough around the edges. At times, she can come off as bossy or domineering, but I see through that – she’s someone that has a real heart and comes from a great place. Anyway, Yvonne hasn’t had much luck with men. It’s been years since she’s had a boyfriend and I think it’s also been a while since she’s been with someone physically. I’m somewhat attracted to her physically and sometimes I find her a bit over bearing, so I debated whether to propose a “friends with benefits” arrangement with her.

A couple of nights ago, we went to an event together. When we talked during the day, she told me how she had done her hair differently and that I might not recognize her when I see her. I joked with her that I’ll just look for the hottest woman at our meeting spot and I’ll start chatting her up and trying to get her number – I think she really liked that indirect compliment.

On the way to the event we did our usual non-stop talking – open, honest, funny, real – just having fun hanging out. I thought about the possibility of doing a friends with benefits arrangement with her in the past but have always stopped myself because I thought I wasn’t that into her or that it could get complicated.

Anyway, we were talking about our personal lives and she asks me if I’m seeing anybody right now. I tell her about my blind date from hell and how I’m just dating right now. She asks me what exactly that means and I just say I’m going out with different women. She digs further and asks if that means having sex with women, too, and I just answer with “if there’s a mutual desire for that kind of arrangement”. Later on, she boasts how a guy recently made a pass at her and how she rarely gets guys making passes at her. Personally, I think guys don’t see beyond the walls she puts up around her and because she’s not gorgeous or pretty in the traditional sense, they don’t pursue her. Inside, I’m thinking that it’s really too bad this woman doesn’t feel desired and sexy because she’s got a beauty about her that’s just not immediately evident. I joke with her that she needs to get laid and she complains that it’s been ages since that’s happened. As I’m wondering whether this is an open invitation to pursue things further with her, she adds, “But I can’t just have casual sex with someone. It’s all or nothing with me.”

On the way back from the event, we take the subway together and continue joking around and talking. In the back of my mind I’m wondering whether I should just do it and make a move just to see how she’d react. I’m not getting the same signs Angela gave me when we first got together for coffee, but at the same time she’s continuing to talk a lot about herself and is really opening up emotionally. When we get out of the subway, we get into her parked car and continue to talk. She’d doing most of the talking (about how she doubts her own abilities) and I’m just sitting there half listening and half wondering what it would be like to just kiss her. Finally, when she’s paused for some breath, I start moving closer to her and getting ready to kiss her. She reacts with “Whoa! What are you doing? Were you about to kiss me?!” and gets a surprised and weird look on her face.

At this point, things could have gone in a couple of directions – the awkward or the laid back route. In previous times, I might have felt unsure of what to do next, but tonight I just reacted in an easy going and laid back way. I treated the whole incident like it was no big deal. Now if I reacted by getting all embarrassed or self conscious, she would have felt really awkward and the evening would have ended on a down note. This way, we just continued talking and she now knows that I find her attractive and am open to the idea of being physically intimate with her. Knowing that she’s desired by a man (i.e. me) gives her a high so I think she feels better about our interaction.

When she asked me “What are you doing?!” as I was going for the kiss, I just replied with, “I wanted you to know that you are desired and that I find you attractive and that I think you have it in you to succeed.” I meant that and I wasn’t just trying to feed her a line. I guess I wanted her to know that she’s got a lot going for her and she should believe in herself more. I also knew that she doubted her own beauty and I wanted to reaffirm that in her.

We continued talking and she dropped me off at my car and I bid her farewell. I think things between us are back to normal and I really don’t think they’ll be any weirdness that often results after one side makes an unreciprocated overture.

I guess I feel that every woman I interact with should feel respected and positive about the interaction. I didn’t want her to think I just wanted to get laid and nothing more. The truth is, I really wanted her feel desired sexually by a man. Maybe that scared her because it’s been a while since she’s been physically intimate with someone. Either way, I’ve put my intentions out there and we’ll see if anything develops.