Casual Conversation

I have a really hard time setting boundaries, and will quietly sacrifice my own happiness and sanity to make others happy. I also have a long history of fearing being alone...

From Freshman year of highschool to 2 months ago (2006-2025, wow almost 20 years, time flies), I think I have been single for a combined total of maybe a year, year and a half? I dated 3 women in a row for a little over 5 years each, exiting one long term relationship and immediately starting another one. Each time I just quietly sacrificed and changed myself for years until I could go no further, and crashed out, super unhealthy. The last long-term relationship, we moved in together after 3 months, and lived together for 5 years through 5 moves and COVID, it was crazy.

After that last long-term, I tried dating more casually, but quickly ended up in another relationship that lasted almost 2 years, but she really hurt me quite a lot, and I was so unable to leave until I was literally hanging onto sanity by a thread, because I was so afraid of being alone.

I told myself after that, I was done with dating... but I quickly fell back into it, and actually succeeded in dating casually for a bit. I ended up with a really pleasant friends-with-benefits situation with someone who had their shit together and was really good at setting boundaries, which helped me immensely, and I started working on myself in my own space outside that. Of course, though, I met some other woman who I fell for, and started dating her exclusively. She did not have her shit together, and I found myself right back in my old habits of sacrificing myself to help her. This lasted another year and a half, until 2 (maybe 3?) months ago, I finally just dumped her because I was so so bored and so tired of sacrificing my own happiness. I even got to the point where I was able to articulate and communicate my needs and wishes that weren't being met (which was a first), but after multiple talks, and almost breaking up once, she just never changed. This time I am REALLY done with dating.

I'm only just now starting to miss the physical side of dating, and would like to someday maybe find a similar FWB thing, but for now, I haven't even thought about setting up a dating profile or trying to meet anyone with the intent of dating. These past months have been the longest stretch in 20 years that I haven't thought about dating, tried to date, set up a dating profile, etc... It's kinda sad when I think about it. I've made a lot of progress on the fear of being alone, and even though I have no pets and live alone in a tiny apartment, I am finding my own happiness and keeping the loneliness at bay with the most active social life I have ever fostered, so for now it is going really well.