Hey all, first time poster here...
I'm 34 years old and I'm your basic nice guy who is not a skirt chaser and therefore always finishes last. I'm also honest and straightforward which in my experience with dating tends to be about as helpful as a bad ankle injury to a basketball player.
Yesterday I went out with a woman I work with. It took me a long time to get around to asking her out because of a couple of rules I'd had in place. 1) Don't date people you work with. 2) Don't date anyone more with an age difference exceeding double digits.
She's 23. She was interested in me and I in her, but I happened to know how old she was and my age never came up in conversation. It just so happens that I look a lot younger than I am. Most people are shocked when they find out how old I am. In fact most guess that I'm in my early to mid twenties, so I realized having never mentioned my age that it's likely she thought the same thing.
When I finally decided to change the rules for this girl, she seemed very interested. We decided to go out for dinner yesterday but she had a night bike ride thing to go to which would cut the night short.
The entire time over dinner I was internally debating myself over how or whether or not to broach the subject of my age. Being the honest, straightforward and respectful fool that I am, and being that it was an issue I had to let go of myself, I felt I owed it to her to let her know how old I am.
Finally, at a point in our conversation, nearing the time when she had to leave for her bike ride, the conversation came around to these teenagers that were hitting on her, and she mentioned her age to point out how silly it was that these younger guys thought they could hook up with her.
Well at that point I went ahead and asked her if she knew how old I was. She said no. I asked her how old she thinks I am. She said she had no idea. I said I'm older than I look. She asked me how old I was. I told her. She said "Wow, you are older than you look."
And suddenly she was in a big big hurry to leave to get to her bike ride thing. The date ended so rushed that I couldn't help feeling like I blew it by telling her when I did. Or it could have been that she was genuinely in a hurry to leave (she'd mentioned she would have to leave for the bike ride when we agreed to the date).
At any rate I'm not sure what to do next. My honest nice guy instincts tell me that I should tell her it took me a while to ask her out because I had to get over the age thing myself, but she is so smart and beautiful that I changed the rules for her and her only. But my brain tells me everything about being an honest nice guy is wrong for dating. I suppose now it's too late to turn back though.
Another problem is that trying to get her on the phone has been a chore. She'll only communicate via text messages. She told me she hates talking on the phone. It so happens that I really dislike communicating via text message (though I do anyway because I know so many people who prefer communicating this way). I'd really have a hard time trying to tell her how I feel over text messages. It just feels wrong to me. But I know I won't get her on the phone and if she's weirded out by the age thing I may not get a second date. The other option would be talking to her about it when I see her at work which would be hard with other people around.
At any rate, thank you all for reading this long rambling tale and I welcome any advice you may have...