I'm [23m] quite dissatisfied with my non existent dating life

Reply Wed 8 Jun, 2022 07:33 am
I’m 23m and I never had a real girlfriend before. I’ve been on a few dates here and there in high school (mostly with girls my mom [49f] lined me up with), and I occasionally had sex with women I met at bars shortly after my 21st birthday. Even then, nothing really came out of those high school dates, those bar hooks up were just one off one night stands, and I don't do them anymore after some pretty bad “near miss” situations that I almost got myself into.

For reasons I don't know how to express with printed words, I just never had the drive to pursue fully committed relationships. Even with girls that I’m attracted to, I just can’t push myself into asking them out. My sister’s sister-in-law [22f] was one such person that I really liked, but I was never able to summon the nerve to call her up on a date.

It didn’t help that I could tell that she didn’t feel that way for me, and thus wasn’t worth pursuing things further than that. She ended up getting together with my brother [28m]. I also don’t know if I’m able to handle the amount of work it takes in maintaining a relationship. Additionally, my job demands that I work long hours, and much of my freetime is taken up by my classes. Thus I often don't have time to go out like that. Last but not least, I’ve tried Tinder, Plenty of Fish, and other dating apps, but the monetization and catfishers drove me off it.

Despite what I’ve stated in my previous paragraphs, I’m far from swearing off dating. I often fantasize about getting married and starting a family of my own. However, due to my aforementioned problems and other pressing issues, I just don’t see this becoming a reality anytime soon.

What brought this up was a conversation I had last Saturday at my sister’s [25f] in-laws’ house. I was with my siblings (including my maternal half brother 28m (whom I brought up earlier), my paternal half sisters 19f and 13f, and my previously mentioned full sister 25f), my sister’s husband (24m), and his siblings (the aforementioned 22f and 15m). While we were watching Netflix, my sister’s little brother in law turned to me, and asked for some dating advice.

He has an ex-girlfriend who is really “special” to him, and they’re apparently talking about getting back together. He wanted to know the best ways to avoid “messing things up again”. As I made pretty clear in this post, that is far from my area of expertise. I wasn’t able to give him anything beyond a weak “just go talk to her.”

When the kid tried prodding further, I flat out told him that I had never been in a relationship before. He, my brother-in-law, my sister’s sister in law, and my youngest sister were quite surprised. They started asking me questions about my stagnant dating life. I told them about with my problems that I discussed in this post.

I was then showered with dating advice from pretty much everyone in the room. My brother, my sisters 25f and 19f, brother-in-law, and my sister’s sister-in-law started throwing around people who they thought would be perfect for me. They settled on one girl, a mutual friend of my older sister and her sister-in-law, and I agreed to it. My sister told me that she’ll have it all arranged.

Their friend texted me the next day, and we agreed to go on Friday evening. I’ve seen this girl in person a few times, and I think she’s really cute, but I never had much of a conversation with her before. Thus I don’t know what she's like or what to expect, and I’m a bit nervous about that.

From what I described here, what are some things I could do to overcome my dating issues? Any sort of advice would be appreciated.

TL:DR: During a discussion I had with my siblings and my sister’s in-laws', I realized how dissatisfied with my non existent dating life. However, I just don’t know how to break through my issues causing it, and would like some advice here.
Reply Wed 8 Jun, 2022 10:56 am
It seems to me that you've put physical and mental barriers in your life so you don't have to date. If that's really not what you want then make an active plan to actually do it.

Set aside every Saturday as Date Night. Make a plan on one of those dating websites you're on and ask someone out. Set up a meeting place and a time, either they show up or they don't. At least you're making an active role in your own life.
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