Hello!
A little background to start... I'm interested in a woman that I used to like back in high school. We were good friends, hung out often, etc. I felt like we had a good connection so I asked her out, she told me someone else had asked her out first just the day before. It sucked but I didn't beat myself up too much about it and we remained good friends. I still felt there was attraction between us but she was a loyal girl and I was just too much of a punk to make any type of advance on her. That relationship lasted way longer than I thought it would and he basically brainwashed her into not having any guy friends. I had told her this guy isn't right for you but I also didn't let her know how I felt about her. She eventually married the douchebag.
Fast forward 10 years, I found out this woman got divorced over 2 years ago and this guy just treated her like shit (as I knew he would.) She started working at a new company, a guy was interested in her, she didn't want any relationship but he was persistent and she married him late last year. When I first contacted her I originally wanted to know how she was doing, you know, small talk. She was happily married and whatnot. I kept texting her maybe trying to see if I could get that connection back. She pushed me back. I took it slow. I eventually asked her to meet up for lunch. Lunch went well. She looked like she hadn't aged, she looked great but I didn't feel that attraction that I felt back then. We kept in touch. I kept trying to make her more comfortable to talk to me. Poke fun at her and try to flirt. I'm really not that good at flirting by the way... But eventually she was receptive. She opened up to me that her marriage isn't going well, that he smokes cigarettes and drinks, and that he hasn't had sex with her since December of last year. She felt unattractive. I reassured her that she's beautiful and that he's crazy for ignoring her. I talk to her about hanging out again, she tells me her schedule and when she gets out early from work. I make it work around my schedule. I find out she likes to smoke cannabis and I invite her over to my place, she was hesitant at first but she comes through. She said she wanted to eat healthy so I had made some salmon the night before and just reheated it, made salad, made some green tea, pretty much catered to her. I felt that she was comfortable and we smoked, got high, talked for hours. She had to go back home to her husband. Less than 5 minutes from leaving my place she texts me that she misses me already. I text her back saying I missed her as soon as closed the door. I felt the attraction this time. It was the same as when we were young. I start being more flirty, sending her some songs, and she was receptive. I invite her to come over again a couple of weeks later. We get massages done, picked up some Mexican food on the way back to my place, and smoke some more cannabis. I still felt unsure of how she would react if I told her how I felt or if I tried making a physical advance on her. Before she had to go again I wanted to tell her how I felt but punked out. We had a long hug and she went home. I couldn't stop thinking about her and told her the next day that I really liked her. She told me that she liked me too and that she used to like me a lot back in high school as well. She said those feelings came back to her and I was excited. I amped up the flirting but our conversations were never really sexual. I didn't really know how to get there. Still don't really. I asked her to go on a real date with me, at night. She accepted.
Fast forward to last week, so I have this really bad thing about overthinking things and felt like the only reason she liked me was because she wasn't getting attention at home. I didn't want this woman for sex alone. I wanted something real. So I kept questioning everything and eventually broke her to where she questioned it too. She told me that I might be right and that she needed to take a step back. That's when I realized I fucked up. Why couldn't I keep my fucking mouth shut?? I don't know why I felt the need to be reassured that she was interested in me when it was all going well. She said she would not bail on our planned date. The next few days felt like hell because the texting was limited and short. I had to convince myself that once she sees me again she'll be sure of her feelings.
We went out for dinner this past Saturday, she looked stunning in a summer dress. I had never seen her so dolled up before. I tell her how beautiful she looks. She's receptive. We have a great time talking, laughing, having some drinks. The restaurant closed at midnight and like the idiot that I am, I didn't think of a second venue to take her. So I ask the stupid rookie question of "what do you want to do now?" And if course it was answered with "I don't know, what do you want to do?" I was like fuck I didn't think this far ahead then she suggested to go to a chocolate bar. We get there and she's more relaxed on her food choices. We talk some more, have more laughs. Then that dreaded time came where she had to go back home to her husband. I needed to know how she felt, she told me she doesn't know. I wanted to kiss her but I'm not spontaneous enough to go for it and tell her instead that I want to kiss her and maybe it'll make up her mind, she replied back if I really wanted to kiss a girl that was confused. She said she had a great time and enjoyed my company. We hugged for a long time. I should have kissed her cheek at least or something!! She got into her car and went home and I'm just there thinking why the fuck did I not try anything!!! What the fuck is wrong with me??? There's an obvious interest in her and I'm not fucking confident enough to pull the trigger!! Why!? I don't know how to overcome the physical barrier. I wanted to touch her all night and it just didn't happen. Would the date have gone different if I didn't break her? Would I feel more confident knowing for sure that she wants me? Too many what-ifs now...
It's easy to say to just go find a single woman but it would be the same thing. The problem is me overthinking shit. I've had dormant feelings for this woman for over 10 years so I'm not really interested in anyone else unless I know for sure that it's not going to go anywhere....
