[25M] My dating history, what am I doing wrong?

Okay. It’s a long story but I’ve been overthinking about this for months and I can’t seem to stop. So I guess I’ve come here to take advice on what exactly am I doing wrong?

Girl 1:

I’ll start from college. In my second year of college, I started talking to this girl. Not that good looking but the purest soul I met in life. She reached out to me regarding some study related stuff and we started talking from there. Few months later, she confessed that she likes me and I also liked her, so we got into a relationship.

Now personally, I’m a physical fitness guy like I like bike trips and treks and she was into it as well. We stayed together for 5 years and eventually broke off because she was overweight for years and could not fix it which caused issues. I know you can judge me, that’s why I’m confessing everything here.

After the breakup, I could not do anything for the next 8 months. Affected my work, health, fitness, everything. Eventually I decided I’ll change and started going to gym and focused on work as well. After a while, I thought let’s look for someone now and I knew dating apps were a disaster so I looked at people offline.

Girl 2:
I liked this girl from office. So, one day in gym I made some talk and eventually we started talking. We spent a lot of time together. However, I was always scared to tell her anything because I never got any signal that she was into me. Months passed, eventually I realised that she always liked someone else and I was kinda a friend only.

Fucked up thing is, we have stayed up together whole night just the two of us and talked about really personal stuff. But still, she never gave any signal that she was into me.

Eventually, I stopped hanging out with her. We still eat together with friends almost 2-3 days but still, my feelings for her went away.

Girl 3:
I don’t really know a lot other people and even my mutuals are all guys so eventually I decided to open account on Hinge. Asked a friend for help and took HingeX. Surprisingly, I got a lot of matches there, approximately 50 matches.

Most conversations were dead, however I did talk with few good people. One of them was this girl from my same hometown, kinda cute, mostly hot. We talked for a while on the app, eventually moved to insta and I asked her out on a date.

This was my first date after a long time. So I took her for coffee, we talked till 12 at night, I took her out on a night bike ride and eventually we came at my place, talked again till 5am and then I dropped her home.

We kept talking and then I realised that after a year or so, she’s planning to move to another city. I’m not really the hookup kinda guy and I don’t like wasting people’s time. I planned another date and in that day, I kinda told her that I can’t be in long distance relationship so it’s best to end things before they get serious.

She still asked me to be her friend, for which I agreed. But the next time we met, I could see that she was getting attached. For her sake and mine, I told her that I can’t do this and that was it. We stopped talking.

Girl 4:
Another girl I met on Hinge, from Mumbai, didn’t really seemed interesting in talking but still the conversation was there. We talked for 2-3 days and I asked her out.

We went on a date, talked again till like 11pm and I dropped her at her home. In her words, she said she was interested and would love to go on a second date.

But because of her work, we could not meet again for few days, we still kept talking but the conversations did not seem like they were coming from someone who was interested in me. In her defence, she did say she was not a chat person. We finally went on a second date, talked till night, took her back to my place, she met with my roommates and because she had a flight to catch the next day, I took her back to her place. We had coffee there and I went back home.

After this, she went to her hometown Mumbai and eventually the conversations slowed down till the point we stopped talking.

Girl 5:
Another girl on Hinge. We were talking, the conversations were good, she was cute and smart, a small influencer passed out from IIM, we talked and I asked her out on a date.

To which she said, she has done this a lot but because most dates go nowhere she would like to talk more first maybe on calls, etc.

Boy was she right. While talking more, she told me she had been in a FWB situation before which is a big no no for me, along with smoking. So I told her respectfully that I can’t take this forward to which we both said our goodbyes and I unmatched her.

Girl 6:
She saw that I liked trekking and reached out on Hinge. We started talking and it felt so easy to talk with this one. She was showing interest, initiating conversations and was just so cute. However, I had a trip planned in some days and knowing what happened with Girl 4, I asked her to meet. She was busy as well so we decided rather than going on a date, let’s meet casually. We literally met first on our pajamas.

We talked, I was into her and for the most part, she seemed interested as well. I thought things were going fine but knowing that there is a trip coming, I knew where things were going.

I tried to keep the conversation going, and it did but again, the replies were coming after a day (to which she said she has too much work pressure), eventually before I even came back from the trip, she got the relocation to Mumbai (she told me she had been pushing her manager for this for a while).

Knowing this and knowing that maybe she’s not as interested in me, I cut off the convo. We said let’s meet before you go back but the day never came.

Girl 7:
A doctor preparing for NEET PG, matched on Hinge. At first, she seemed interested but because of her exams, just super super busy. Now by this time, I’m frustrated and I’ve decided to relocate to another city as well. I told her the same to which she said she’s okay. We still kept talking and one day she asked me out.

It was very last minute and we met, to my surprise, she was the most interesting person I met till this time. I liked her, we talked, had good time and eventually said our byes. I don’t think she was interested in taking this any further given I’m moving and I felt she was not into me after we met because we have a very different upbringing.

Girl 8:
Frustrated from the apps, I decided to delete them and just stop searching. However, loneliness creeped in and this time I decided to post on Reddit. To my surprise, few people reached out to me.

From all this, there was this girl. She seemed sweet and a kind person, we talked for few days and decided to share our socials. Here’s the thing with Reddit, you don’t really know who you are talking with. While the girl was really nice, I was not physically attracted to her. So I told her straight up that this is the case, and we kinda stopped talking from there.

Girl 9:
Another girl from Reddit. I think this one was my fault because I pushed her too much towards what you want to do it life and just boring stuff because honestly I was done by this point. But still we talked for a while and the conversations were okay. However, she smokes weed which I’m not comfortable with, so this was never gonna work. Eventually the girl told that we are incompatible and we stopped talking from there.

This was it.

I deleted the apps, stopped all convos with everyone. People tell me that I could have hooked up at least with some of them but I don’t know. I’m just not that guy. I guess things really have changed.

To my surprise, the relationship I had in college with Girl 1 was the best one, I was never able to find anyone after that. Maybe I will someday but honestly, I regret that I broke up with Girl 1 and the guilt is just never ending. I guess I’ll have to life with it.