So I've dated off and on for sometime now. I'm 32 (M), generally friendly and good looking, good physical shape, all of that stuff. I'm not a high income earner but I'm well on my way of fixing that (was supposed to get promoted at the YMCA before Covid-19 hit). I'm a personal trainer and I also work retail, which is my current "essential" job which I'm thankful for.
I have always had problems with women. I was both shy and awkward for a long time, and didn't lose my virginity until I was 24 through a mutual friend. I didn't have sex again until I was 28, to a girl I also met through mutual friends and to whom I fell in love with. We had a great time for the first 2 months and got a few great sex sessions in with her, but she didn't want a relationship - she wanted to keep "talking" though. Well, the sex ended and after about 5 months she dumped me. I'd rather not go into too much detail but she was the only one I was ever in love with, and she would eventually tell me that we couldn't be friends. Admittedly, my desperation, clinginess and nervousness didn't help me at all. It's been over 3 years and I'm still not 100% over it, and I miss her a lot.
So since then, I've had about one sexual encounter a year, usually during the summer. I've had a few dates in between, but almost all of the time they end up going nowhere, or I did something to sabotage it. I feel like I've gotten more confident over time talking to women, but I also feel as though I'm still doing something to self-sabotaging myself.
One of the "blind spots" that my roommate pointed out was that I was very close and clingy towards one girl that hung out with us on a boat at the lake last year. I took heed of his advice and have been careful about that since, but now recent encounters with women have suggested that I have a another problem.
When I'm talking to a girl and I feel like things are going well (I'm sitting close to them and we're alone), I'm extremely hesitant on touching them beyond the knee, shoulders or leg. Past experiences have taught me that I have to see really obvious signs before I can touch a girl by her vagina or breasts. Honestly, I have only fingered a girl a few times and I honestly don't know what I'm doing. My roommate explained it to me but it sounded like a confusing step-by-step process.
So before the pandemic got bad, I managed to have a chance at hanging out with two seperate women. One of them was one of my neighbors in my apartment building. We knew each other for a little while now and she started inviting me over to drink and watch TV with her. I was there on about three occasions, and I knew that she likely wanted to be with me for a specific reason. At one point, she was about to fall asleep one night and reached out to me and grabbed my shirt, like she was about to kiss me, before landing back on her couch and going to sleep. We hung out again two more nights and sat on her couch drinking and watching Netflix but I was too afraid to make a move.
The second girl was a friend of my best friend's girlfriend that came to visit from Florida. I came by his house and we all played drinking games and sang karaoke. We ended up sleeping on opposite ends of the couch, but later on I went to the spare bedroom because I was having trouble staying asleep (she was currently staying in there but my friend said it was cool to crash in there for awhile). She came up not long after, and asked if I could put some kind of icy-hot style lotion on her back, and she did the same for mine. She then went to her side of the bed and we proceeded to lightly cuddle, not sure whether or not the possibility of sex was imminent. I touched her breasts lightly and her waist, but I didn't go down to her crotch area - I was hoping she would make a move back but didn't. So I went back to my side and slept. I told two of my friends about what happened and they said that I should've done more, and that her being in the bed with me was a definite good sign. She would eventually hook up with another of my friends who has rockstar confidence compared to me, even though I'm the better looking guy.
I feel like I have a problem sealing the deal with women physically, like something is pulling me back. I don't have a history of sexual abuse or anything of the sort - just some bad awkward experiences with touching women. Nothing crazy or in the realm of sexual assault, but enough that it might be keeping me from getting too physical. I've noticed now that I've actually had a few encounters with women in the past where I didn't capitalize because I was either too stupid to know or I was nervous. I feel like I've been trying for years to get laid or get a girlfriend and I'm only now understanding the "game".
Sorry for the long post, this seems to be a bad tendency for me but I like going into detail. Should I talk to someone about my problem? I thought about seeing a therapist about it, I had one after my breakup and I felt like it did some good. I know I shouldn't worry about dating and sex right now during lockdown, but I would like some possible answers as to what to do once I CAN start going out and date again. Thanks for reading!
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