Here's my situation. I hope I can get some help from you. Also, general background, I tend to binge when I drink so you can assume for most of the following she or I or both of us are dealing with being at least somewhat intoxicated which I know is a big part of my problem for sure.
I am a man, early 50s, divorced 10 years, 1 adult daughter
She is a woman, early 50s, divorced 6 years, 1 teen son
We met on a dating site around 5 years ago. At the time we had a couple of good dates, but I did not feel like I wanted more than friends at the time. This sounds really weird in retrospect, but it was a stupid, superficial reason now that I think back. She bore a vague, passing resemblance to a woman at work whom I disliked. As I said, a weird reason but I guess I fell prey to first physical impressions.
(On top of that, I was getting out of a one-year relationship with a woman who had said she wanted kids, and at first I thought I could have another kid. But when I backed off from that, things fell apart. She and I had sexual chemistry, but it was never destined to become anything like a long-term relationship or marriage.)
She later told me (back to my current "she") she thought, "I don't need any more friends, but I appreciated your honesty so I agreed to be friends." We kept in touch loosely but went on with our parallel lives. Due to that one-year relationship that I mentioned, I honestly was not eager about dating anyone, and I gradually had been moving into a bachelor/hermit/barfly life. Not good, but the only reason I say that is that I have tried to tell her that my initial friendship thing was not a typical "friend zone." I really did enjoy her company and even told her that I could see it someday leading to more.
Fast forward again to 2019. I was at a bar watching sports with a friend, and he told me he saw a woman who kept looking at me. She was with a guy. When I finally peered into the dark bar atmosphere, I saw that it was HER. My friend told me to go over and say hi, but I said no, she's with a guy. However, as my friend and I left, I waved to her and she smiled and waved back. Later that night I texted her and we reconnected. Somewhere around that time she says she broke up with that other guy.
From that time until a month or so ago, she and I started meeting up more and more and texting more and more, including FaceTime when she was traveling for work. Finally, when we were at dinner one night, we had both had a bit too much to drink, and she leaned in and kissed me. I returned the kiss, it was great. I panicked and did not want to hurt either of us, so I kept being reluctant. It's painful to recall this because this was the point where I could have chosen a different path. And maybe talking to her about my money then would have allowed her to be supportive without pulling back.
But I kept vacillating on asking her to be my girlfriend, this time for a different reason. Due to the pandemic I gradually fell behind on rent and now I owe a lot, over $15,000, which I am trying to figure out how to pay off or negotiate some kind of exit from my lease.
I bring up the rent because my vacillating ended around March of this year, before I told her about my money problems, but after I decided that my feelings for her had grown too much for me to keep saying I wanted to be just friends. The time we spent together had drawn me out of my loneliness and was of a completely better nature in terms of our sharing time together, sharing conversation time, mutual attraction, and on and on.
It got to the point that she was sending me so many sweet texts and GIFs that she was thinking about me. She invited me over to her apartment on several occasions. On one night she started feeling me up and took me to her bedroom and we made love. That happened one more time there, and then another three times at my apartment. We held hands, kissed, shared walks, day trips, she had me meet her sister and her kids and a few of her other friends (she was upset that I had not introduced her to my daughter though). I would usually take her home at the end of the night (more later) and we would kiss passionately before saying goodnight. Pet names, lovey-dovey GIFs, the whole nine yards, practically.
Then it changed.
First, she started talking more and more about traveling, and I kept trying to tell her that I did not have money to travel. Finally I had to admit my money situation. She was taken aback but was supportive at first, even offering me money to help pay. I refused, I didn't think that would be a good idea at all and she would either resent me or lose respect (she lost respect anyway, see below).
Everything seemed to have stayed the same until the following weekend. First, we met up at my local bar, and she seemed tired. She said it was work, which was probably partly true. But then the bar manager asked if we could move from our table to the bar so they could seat a larger party at the table. We said sure and moved. At the bar was this weird guy whose talking style I couldn't follow. His friend came over, a guy I had randomly made friends with before over a football game. That latter guy is always glad-handing at the bar and struck up a conversation with her right next to me. Apparently they went to the same area Catholic grade schools. As they got into their conversation, her body language moved away from me (usually she was all over me). Then, he said he had to get her number to invite her to a party the next day and so they could catch up about school and the neighborhood. She gave him her number right in front of me.
I didn't say anything in the moment except to say "hey, we're all adults" when he made some disclaimer about why he was asking her number. But when we left I told her I felt like a fool and why did she do that. I am not good in arguments, but verbally and via text I basically said how would you feel if I did that to you? She said:
"I'm still perplexed by what happened tonight. We can go back and forth, and I can continue to try to explain myself as to why your position is misplaced, but I think it we will go in circles.
Thus, I will accept that your feeling were hurt some how despite the fact that I would never do such a thing intentionally. So I'm sorry because despite the fact that we are not committed and I have the right to explore, I am not that girl that would try to purposely make you jealous nor hurt your feelings.
I did get upset at the end with your *** for tat suggestion, and Yes, I would get upset if you took some women's number. "
To me this sounded like (1) sorry if you're offended and (2) trying to have her cake and eat it too - specifically, "we are not committed," yes but we have done all those couple things I mentioned above, so doesn't that warrant a little respect about handing out our numbers to people in front of each other? Moreover, if "we are not committed," what right would SHE have to get upset if I took some woman's number?
Anyway, the next day we texted a bit more and then she invited me to a professional meetup party she was at. I should not have gone, but by this point I was getting more and more feelings for her and we had entered this odd dance of approach and avoidance. I drank at the party and struck up a conversation with a pretty woman there (which is funny because my "she" made a point of telling me I had done that) - she barely talked to me at the party, which I guess is ok because it was her party. Then we joined some of the people who left the party and went to a restaurant.
There, she was initially seated across from me but they moved her to the head of the table, where she went on a little speech about what she wanted in a man. A guy there started professing how if HE were with HER, he would give her all of those things. He raised a toast and she toasted back. When it was time for everyone to leave, I naturally assumed I would walk her home alone as I usually did. But that toasting guy suddenly decided that he and another guy should also "help" get her home. She agreed, at which point, hot blood ran up into my face and I excused myself abruptly and left all of them. I cried all the way home and when we FaceTimed about it, she retaliated with all the times she had cried about me when I said "just friends."
We met one more time in person before she went away on a trip with her son. We still argued over the whole friend/respect/jealousy thing. She accused me of "dating" my "other girlfried" (wait I thought we were not committed) - by which she was referring to a woman I went on 2 dates with over the course of 18 months and whom I did not want to be my girlfriend. We both left angry and she refused to let me walk her home.
At that point I spiraled into a deep funk. Although she texted a few times that gave me hope, I got drunk a few times and sent her streams of overly emotional texts starting in angry/demanding mode and devolving into begging/pleasing mode. This has happened to me twice before and both times the women blocked me. But she has not blocked me which I find strange because she would read my messages and not reply, but not block me either. Is she just torturing me?
Now we have reached a numb equilibrium. I wrote her a 4-page heartfelt letter where I pleaded my case. I know men are not supposed to do this, according to the dating sites and coaches. But I just wanted her to see what I was thinking. She has not even acknowledged that I sent it, nor said even one thing about it. She has repeatedly insisted that it is not about the money, but the timing seems way too coincidental and she also has gone silent about almost everything except switching to "we don't have the same interests or want the same things." So who knows.
She has sort of agreed to meet up and chat about this. But as I expected, she bailed out yesterday saying she is busy with work and she has plans for the weekend. I am now obsessed. I really don't want to know about her dating other men, but I also can't help wanting to be her man. So I am having awful intrusive thoughts about her going off for the weekend with some new guy she is with.
This is so painful. It's not just that I don't want to be alone, I have done that before. It is that we spent so much time doing things and going to places all around where I live and hang out, so EVERYTHING reminds me of her, and also because of my money problems, I feel worthless and that no woman would date me, while she is off probably collecting dates by the armful. She even told me she has already been on a couple of dates - less than a month after she said her desire for me was multiplying. I have spent time walking trying to burn off the anxiety and pain, but only recently have I been able to go more than 2 days without breaking down crying. Every time I want to turn around and share some meme or article or news I realize it's pointless, along with the hope of just seeing her and holding her again.
Anyway, I always try to write short posts but they always end up too long. I hope someone reads through this and can offer me some advice. I know the drinking is an issue, she used it as another reason why I was crossing her boundaries when she had respected mine as a friend (she is right about that part). Some days I want to block her and remove all traces from my devices. But then I get really sad and can't go through with it.
Thanks for any help.