callibaetis Posted July 12, 2009 Posted July 12, 2009 I'm a single man in my mid-40's and have a female friend who is in her mid-30's. I know her ex-boyfriend quite well, and she knows my ex-girlfriend, so we had common ground right off the bat. We started "seeing" each other after running into each other and complaining over a beer how much it sucks to be single in a small, gossipy town. So after six months of seeing each other as friends basically weekly for dinner, my perspective is changing. I really like her and am interested in exploring a more romantic relationship. To this point, I have done absolutely nothing to tip my hand - In fact, in the beginning we both expressed our desire NOT to be in a relationship with anybody (well, I told her I am good with it 80% of the time but that there are times when I want someone to come home to). Other than hugs I have not initiated any physical contact. She knows through the course of conversation that I think she is gorgeous. Other than the first dinner when we vented about our respective exes and that this is a bad place to be single, we have not talked at all about our dating - I know though the grapevine that she occasionally goes out on dates and I'm sure she knows the same about me, but we never bring it up with each other. My reason for not doing so is that I want her to see me as available. I don't know why she never mentions her dates. So now we have a quick road trip planned to the big city in a couple of weeks to do something cultural and have a great meal. We have not made the lodging arrangements and I'm not that concerned with it, but I'm finding myself looking at this as a date and not two friends going to dinner and the theater. We'll have a lot of time on the road and I am sure the conversation will go many different directions, but I'm wondering if I should just confess to her that while I entered this thing innocently enough, that the more time we spend together the more I wonder about the romantic possibilities. This is the typical "I don't want to ruin the friendship" scenario, and I'm too damn old to be afraid to be honest...... But it seems I am. Thoughts? Encouragement? Admonissions?
Lucky555 Posted July 12, 2009 Posted July 12, 2009 Just be honest with yourself. really you can't keep seeing this woman and "just be friends" when you know you want something more. So here it is....you can do this face to face or over the phone, "I would like to know if you wanted to go out on a date" SPECIFY DATE. If your not calling your outings as dates then she would get the point here. If she is not interested she will say, "i like you but lets just be friends" if she is interested then she will say "sure." You really have to be honest here. I can't imagine going out with the her and having feelings that she does not know you have, its torture to yourself. Hope that helps
Author callibaetis Posted July 12, 2009 Author Posted July 12, 2009 If your not calling your outings as dates then she would get the point here. Yeah, we have really just called them nothing - just "hey, do you want to come over for dinner?" or "let's go to the lake." It's usually her suggestion to go do something and there have been several things that make me think she may think of me as more than a friend. I wouldn't have let my mind take me here if I didn't think I saw something - been down that road before! Really, I could be fine with just being buds as long as I know that is the score - but I just have a suspicion that we're both playing it cool and I don't want to look back and wish I had asked. We are both admittedly pretty guarded people.....
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