Long story short I broke up with my ex about 6 months ago, had gone through a tad bit of depression, anxiety, and frustrated online dating just did not work anymore. I have lost 65 pounds and have about 35 more to go to get to my ideal BMI. I am also starting to enjoy my old hobbies a tad bit more, and I have continued to work on my investments, and plan to buy a condo abroad, build some storage units in my home town, and eventually get into aviation. Further once things are a bit more settled I would like to start traveling again. In addition, I am working on a programming certificate that can transfer to a CS degree. My current job is not bad, but I would need to move and I want to take advantage of cheap CS degrees where I live. I also plan to travel to Canada and Paraguay this upcoming year.

As far as dating, I have tried international, local, and cold approaching. I did about 57 cold approaches to conquer my anxiety but I think I am going to step back from the 100 approach challenge until I get myself back together. International dating seems like an option but I am taking a break from the apps in general and will resume on international dating once things are a little more clear with international traveling.

I also have been debating how to dress better as I have been leaning towards more collared shirts for work and buying less "band shirts" and the like, but I feel like I could be doing better. I want to represent myself better as a real estate investor but don't want to outshine the boss at work. So dressing better (more than jeans and a dress shirt), but don't want to be a jerk. I am thinking Henleys for going out but open to changing out things, I just don't want to be over the top.

I feel like I am framing my dating struggles correctly. I don't have enough data to go off of (I try to scroll Reddit looking for answers, but it seems like it is stuff that is repeats from before). I have tried to build confidence by doing what I love but real estate investing is not as dynamic as stock investing and I feel like I get more bank for my buck confidence wise from stock trading (which I am good at). However, I have noticed doing stuff I like has made me feel less depressed. It does not boost my confidence, but things like going to a concert, playing a game, and programming (ok that could build confidence), and reading seem to bring happiness, but are not "productive". I know that programming and stock trading are productive, as are my goals, but could the one thing I was missing from the mix be fun? I might invest a bit more in this as time goes on (getting MLB tv), and maybe travel outside the US as things are permitted. I think I failed to enjoy myself and as a result it hit into my happiness. As far as confidence, I am a bit iffy on but I think with my goals being semi tactical, I think I will have enough to go on for a bit. Would there be anything else you would add to this to build myself back up?