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I’m 35 years old and prior to recently had never dated before, and am still a virgin. I’m mildly physically debilitated due to having arthritis in all my joints, am marginally employed in a call center, live with my father, have no social life or hobbies, and am severely depressed.
This year I developed a huge crush on a 40 year old co-worker, but never approached because I considered her out of my league. Suddenly in May, to my amazement, she started chasing me. She sent me a friend request on Facebook and came onto me in a big way over Messenger one night by confessing her attraction to me and all but throwing her vagina at me. It wasn’t clear exactly what kind of relationship she wanted, but it was obvious that sex was on the table.
I deflected her at first because I was timid, but admitted my attraction to her. Two weeks after that FB conversation, I went on my first date with her. Over five weeks, we went out on four 1-1 dates and went out with co-workers together several times (due to her being a single mom, she has limited availability). We texted every day and hung out together at work during breaks and lunch. She seemed to like me for me and was very understanding about my life situation. She was always concerned and caring.
Because of my inexperience with women, I made constant mistakes in dealing with her. The biggest one was that I was timid to the point of acting disinterested. Most of the time I acted like a platonic friend only. I let her flirt with me, but never flirted with her. I was especially shy about sex, and for most of the relationship, deflected her attempts to discuss having it. Toward the end, she stated explicitly that she was willing to take my virginity, and my responses were tepid to negative (on one occasion I even said “I can’t even imagine us kissing, let alone having sex”). There were times I acted needy, beta, pliable, and emotionally weak. There were a few texts I absolutely cringe at reading now where I was just way too nice, and I knew she hates this trait in men.
In July we found out that our workplace would be shutting down and that we would be getting laid off at the end of the month. She handled this a lot better than I did (due to my disability, my options are limited). That month my attitude at work went to complete and utter sh*t, and at the end she made it clear how much this put her off.
One night in mid-July I had been particularly angry about work and quit early after a mild tantrum, which she witnessed. She carpooled with me to work that day, and I asked her if she could find another ride home so I could leave. I ended up waiting in the parking lot for her shift to end so I could give her a ride, but she later told me that she still took great offense to my willingness to ditch her. That evening she had me drop her off at the end of her driveway rather than taking her to the door and told me she was “drained” with my negativity. That marked the point when she went cold on me. After that, she greatly reduced texting with me, stopped carpooling with me, stopped offering to hangout after work, and stopped all flirting. I just went along with it and acted like I was unbothered. For the next few weeks I tried to come up with the balls to do ask her out again, but the writing was on the wall that she’d lost interest, so I never did. Instead, I sent the usual bullsh*t beta male signals that I just wanted to be friends.
Three weeks after going cold on me, she shared in our group text of mutual friends that she was planning to have someone over to her house for drinks and sex that night. She shared this knowing I would read it. I don't know whether she did it to make me jealous or really or really thought I just wouldn't care. It devastated me utterly. In my emotional state, I drove past her house that night, and there was a strange car parked outside overnight. She never confirmed explicitly what happened, but based on what she has said, if she’s telling the truth, I believe she had a sexual relationship with someone that lasted for 2-3 weeks and is now over.
At this point, almost a month later, our relationship is almost nonexistent. She only talks to me when I’m with the group of co-workers, which I have withdrawn from as of last week. I don’t want to be friends, so I stopped acting like one. And she doesn’t flirt with me anymore, so we don’t talk. Last week she called me and told me she could get me a job at her new workplace; I told her I already had another job lined up and that “I’d rather smash my nuts with a hammer for 40 hours a week than work there.” I was just being a smartass, but she took it as me spitting in her face and rescinded the offer, even after I apologized. I sent an apology text three days later and she never replied. We haven’t spoken since and it hurts.
Is there ANY hope that I could ever get her interested in me again? I only hold out hope because she was clearly attracted to me at one point, and the behaviors that killed her interest are fixable. It absolutely eats at me 24/7 that lightning struck when this beautiful, intelligent woman was willing to have sex with me, and I did everything in my power to repel her. I just didn’t know what the hell I was doing, but I can fix these mistakes. I can't stand how bad I f*cked this up.
I agree With some of the others. You mess this up beyond recovery. Still, if you have any shot at all it lies in being something different than what you’ve been. That is, be decisive and assertive vice a Whiney little . So call her. Call her, don’t text. Sound as decisive as you can and tell her you want to try again. If she’s willing to give you another shot arrange when you can get together again. When you do, talk about what’s GOOD in your life instead of being so negative. (Seriously, negative men a huge turnoff to women.)
If she doesn’t give you another shot don’t break down and cry. Acknowledge that you know you don’t deserve it and tell her you hope she changes her mind. Don’t grovel and beg. And if you have to move on donso with the resolve to be a better person. Half your post was you telling your hard luck story as if it somehow was justification for your behavior. I get that all those circumstances can affect your self confidence but truthfully that’s a choice you’ve made. Going forward that’s something you can also choose to change.
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. So call her. Call her, don’t text. Sound as decisive as you can and tell her you want to try again. If she’s willing to give you another shot arrange when you can get together again. When you do, talk about what’s GOOD in your life instead of being so negative. (Seriously, negative men a huge turnoff to women.) 
