Getting back in the game

So, I'm new here, hi!

I'm a 28 year old guy (about to turn 29 in November-fuck) who's kind of been out of the dating scene for a while. I've tried to dip my toes back in here and there, but haven't really taken it seriously. For context, I was dating someone that I worked with back in 2017, she was a mom, divorced, and had dated another guy I never knew about after she got out of her marriage. He was a drug addict and irresponsible from the sounds of it. They lived together for sometime and he helped with her kids (why she let someone actively abusing substances and not being in a stable state of mind around her kids is something that will always escape me). So, he got locked up before her and I started dating, she never mentioned him-not once until close to when he was getting out, and decided she needed to tell me about him in case she decided to let him be around her kids. I was respectful but very, very hesitant. I always knew the boundaries she has as a parent and reassured her that I would be supportive of what she felt would be best for her girls, and that all I really asked was that we could communicate openly about what she had decided regarding him. Her birthday was coming up and I did what I could to make it special since she shared a birthday with her oldest daughter and hadn't celebrated it once since she was born. We got massages, got her closest friends together for a dinner at her favorite local place, and went and watched some fireworks from near downtown afterwards. The next day she was really cold and callous. I didn't understand why until later. The following week, I was working on a day she had off and I hadn't heard from her much. I was a little anxious but just figured she was busy with the kids so I didn't think much of it. I had a break at work and was scrolling social media and saw some posts of hers from that afternoon. She had spent the entire day with the ex that had just gotten out of prison with her daughters. When I got off work I called her, and asked her about her day, she very obviously lied, and I asked her about the posts, she started to backpedal and came clean about what she had done that day. I didn't accuse her of cheating, and it's a bit gray I suppose, but seeing as we had talked about her just letting me know what her plan was regarding him and her kids and keeping me in the loop, and she hadn't done that-I had lost a lot of trust in her. Despite this, I was willing to figure it out together, but she didn't want to and broke up with me. Come to find out they started dating again, and down the road things didn't work out between them for the second time (who would have guessed).

This whole situation really fucked me up. I was convinced that I wasn't good enough, that I had no reason to even bother trying to date again. It'd probably just wind up being another situation that I'd feel taken advantage of and hurt over. I spiraled bad. Started drinking myself to sleep every night, had plans to kill myself, fuck-that was some of the darkest moments of my life. Truly rock bottom. Then beginning of 2018 I sunk even lower. I finally let down my walls and let someone new in, we hit things off and seemed really good for one another but we in different states, so we didn't really move anything forward-just flirted a lot and hung out a ton. It was good for both of us, but I caught feelings while she didn't really feel the same. We stayed friends but I hit the bottle hard again and one night was going to down a bottle of pills and just not wake up. I called my mom to say goodbye, but she thankfully stopped me, I got psychiatric help and cleaned up. I took a year to be sober and get my life back on track and succeeded. I relearned how to make new friends and took a lot of my life online (I started streaming full time on twitch and found a passion in my life again).

Alright, so fast forward to now: since quarantine I've had the (worst timed) itch to start dating again and to put myself out there. The first couple months I started doing a few things for myself, little exercise, better eating, socializing more etc. So I'm in a pretty good headspace now. I figured since I'm not out and about much due to social distancing, I'd look into some dating apps like tinder, bumble, and recently PoF. I also asked out a girl who works where I get my haircuts and she seemed interested but never responded to my messages when setting up the date. I've been talking to a few women on the dating apps here and there, but few have really stood out. One in particular seemed like we clicked. Similar interests, fun conversations, mutual attraction/interest. So we swapped numbers and started texting. Things look good but I want to ease in before going out on a date, so I asked if we could talk on the phone sometime to get to know each other some more. Annnnd ghosted. I know this happens, and it's probably better now than later down the road, but it still hit harder than I expected. I'm really not looking for anything too serious right now, I just want to see where things go, but I can't figure out why I end up feeling hung up after rejection like this. I start to doubt myself again and think that maybe I'm really not good enough, or that my ex had every reason to leave me and that if anything I'm worse off than I was a couple years ago when her and I dated. I know I've still got a lot to learn, and I'm not perfect. Maybe sometimes it's just that things drift off or end up not clicking like they seemed. I can understand that.

I also thinking about possibly moving from the Midwest to the Pacific Northwest in the coming year if things go alright financially for me but that isn't written in stone.

I guess what advice I'm looking for here is just how have you all overcome similar obstacles in your dating lives? How do you approach dating apps, and do you have any input on things I could do to maybe be a bit more successful in pursuing something albeit casual or otherwise?

TL;DR: Went through a shitty breakup, really fractured my self esteem and had to find myself again. Now a couple years later, I'm starting to actively seek out dating as an option, but am fighting some discouragement and am looking for advice on how to go about re-entering the dating scene.

Thanks in advance for reading through this, I know I got a bit vulnerable explaining the context, and some of it's a bit heavy, but I really appreciate any and all input from you guys!

Submitted October 31, 2020 at 12:16AM

So, I'm new here, hi!I'm a 28 year old guy (about to turn 29 in November-fuck) who's kind of been out of the dating scene for a while. I've tried to dip my toes back in here and there, but haven't really taken it seriously. For context, I was dating someone that I worked with back in 2017, she was a mom, divorced, and had dated another guy I never knew about after she got out of her marriage. He was a drug addict and irresponsible from the sounds of it. They lived together for sometime and he helped with her kids (why she let someone actively abusing substances and not being in a stable state of mind around her kids is something that will always escape me). So, he got locked up before her and I started dating, she never mentioned him-not once until close to when he was getting out, and decided she needed to tell me about him in case she decided to let him be around her kids. I was respectful but very, very hesitant. I always knew the boundaries she has as a parent and reassured her that I would be supportive of what she felt would be best for her girls, and that all I really asked was that we could communicate openly about what she had decided regarding him. Her birthday was coming up and I did what I could to make it special since she shared a birthday with her oldest daughter and hadn't celebrated it once since she was born. We got massages, got her closest friends together for a dinner at her favorite local place, and went and watched some fireworks from near downtown afterwards. The next day she was really cold and callous. I didn't understand why until later. The following week, I was working on a day she had off and I hadn't heard from her much. I was a little anxious but just figured she was busy with the kids so I didn't think much of it. I had a break at work and was scrolling social media and saw some posts of hers from that afternoon. She had spent the entire day with the ex that had just gotten out of prison with her daughters. When I got off work I called her, and asked her about her day, she very obviously lied, and I asked her about the posts, she started to backpedal and came clean about what she had done that day. I didn't accuse her of cheating, and it's a bit gray I suppose, but seeing as we had talked about her just letting me know what her plan was regarding him and her kids and keeping me in the loop, and she hadn't done that-I had lost a lot of trust in her. Despite this, I was willing to figure it out together, but she didn't want to and broke up with me. Come to find out they started dating again, and down the road things didn't work out between them for the second time (who would have guessed).This whole situation really fucked me up. I was convinced that I wasn't good enough, that I had no reason to even bother trying to date again. It'd probably just wind up being another situation that I'd feel taken advantage of and hurt over. I spiraled bad. Started drinking myself to sleep every night, had plans to kill myself, fuck-that was some of the darkest moments of my life. Truly rock bottom. Then beginning of 2018 I sunk even lower. I finally let down my walls and let someone new in, we hit things off and seemed really good for one another but we in different states, so we didn't really move anything forward-just flirted a lot and hung out a ton. It was good for both of us, but I caught feelings while she didn't really feel the same. We stayed friends but I hit the bottle hard again and one night was going to down a bottle of pills and just not wake up. I called my mom to say goodbye, but she thankfully stopped me, I got psychiatric help and cleaned up. I took a year to be sober and get my life back on track and succeeded. I relearned how to make new friends and took a lot of my life online (I started streaming full time on twitch and found a passion in my life again).Alright, so fast forward to now: since quarantine I've had the (worst timed) itch to start dating again and to put myself out there. The first couple months I started doing a few things for myself, little exercise, better eating, socializing more etc. So I'm in a pretty good headspace now. I figured since I'm not out and about much due to social distancing, I'd look into some dating apps like tinder, bumble, and recently PoF. I also asked out a girl who works where I get my haircuts and she seemed interested but never responded to my messages when setting up the date. I've been talking to a few women on the dating apps here and there, but few have really stood out. One in particular seemed like we clicked. Similar interests, fun conversations, mutual attraction/interest. So we swapped numbers and started texting. Things look good but I want to ease in before going out on a date, so I asked if we could talk on the phone sometime to get to know each other some more. Annnnd ghosted. I know this happens, and it's probably better now than later down the road, but it still hit harder than I expected. I'm really not looking for anything too serious right now, I just want to see where things go, but I can't figure out why I end up feeling hung up after rejection like this. I start to doubt myself again and think that maybe I'm really not good enough, or that my ex had every reason to leave me and that if anything I'm worse off than I was a couple years ago when her and I dated. I know I've still got a lot to learn, and I'm not perfect. Maybe sometimes it's just that things drift off or end up not clicking like they seemed. I can understand that.I also thinking about possibly moving from the Midwest to the Pacific Northwest in the coming year if things go alright financially for me but that isn't written in stone.I guess what advice I'm looking for here is just how have you all overcome similar obstacles in your dating lives? How do you approach dating apps, and do you have any input on things I could do to maybe be a bit more successful in pursuing something albeit casual or otherwise?TL;DR: Went through a shitty breakup, really fractured my self esteem and had to find myself again. Now a couple years later, I'm starting to actively seek out dating as an option, but am fighting some discouragement and am looking for advice on how to go about re-entering the dating scene.Thanks in advance for reading through this, I know I got a bit vulnerable explaining the context, and some of it's a bit heavy, but I really appreciate any and all input from you guys!