I'm seeking feedback to bounce the ideas around in my head. I'm at somewhat of a cross-roads I feel with my life and decision making and I don't know what my blindspots could be. I tried to give a lot of detail to indicate I value your ideas and for context.

Basically - what should I be prioritizing or doing? Tell me what you would do. I feel an immense pressure due to my age, being single, wanting a family, and that I feel objectively I'm doing pretty well already - it shouldn't be this hard lol.

What's going through my head:

  • Retire in 7-10 years either completely or to some lazy fun job. Save money. Basically never go out of way like I'm doing now. I work in retirement planning and I can do this with extreme confidence. = Deprioritize dating/women?
  • I love nature but live in Chicago. I want to go elsewhere. But this would hurt career and dating options and be more expensive - I can save a lot of money here.
  • Move to upgraded apartment? I live in a cheap place to save money. Fantastic location. I can't justify spending $1000 extra per month for better painted walls and countertop, but maybe women think I'm broke? -Try something new in dating approach? Why do I have such bad luck on dates or do I have bad luck picking them? I used to get 1/3 of girls to bang without any effort 7-8 years ago. Now even if a date goes objectively good, maybe it's 1/4 or 1/5 change to get a 2nd date and it often fizzles then. Is this a change in my age or online dating making women think more highly of themselves when they aren't that special? That I am not bragging about myself?
  • I've been on ~50 1st dates in 18mo so not like I CANT get a date, but it's so exhausting.
  • Should I just de-prioritize indicating that I'm looked for a long-term partner/wife? I don't know it seems like women are absolutely delusional at my age.

Dating history:

  1. Been on ~50 1st dates in the last 18mo. Feel would be WAY easier but I put 'conservative' in online dating profile. Thus these aren't scared of trump supporters.
  2. All dates involve women making 100k-250k, without kids. I'd say typically 130k. I'd estimate almost all of them are like stereotypical - dog+brunch+vacations+wine night with girls+love my nephew+'open to kids'+'love my career'. They are all nurses, CPAs, finance stuff, marketing, software sales...Never fat, all 'love fitness', normal variation in facial looks.
  3. I feel my first date luck is WAY worse than it should be. Am I aiming too high an these girls all are delusional? I'm 6ft, 1mil+ in stocks, 200k+ salary, jacked, etc... but more reserved. Should I be more aggressive or brag about myself?
  4. I typically ask generic smalltalk but indicate I'm serious about finding someone and not trying to waste their time (true). How do I brag about myself without coming across as try-hard? I just talk like a normal person.

Me:

  • age 33. Turn 34 in December.
  • Salary: 213k per year, high stress finance job. Probably would make 175-190k elsewhere
  • Networth: 1075k. No jackpot, no family help. Paid own college. I just invest my money.
  • Looks: 6'1ft, 225LB, 75% white & 25% Brazilian, 505LB parallel squat, 360LB pause bench press, I guess 7/10ish face?
  • Located in Chicago
  • No mental problems,
  • 8 or 9/10 fashion / well fitted, classic clothing.
  • Introverted, but not shy. I like 1-1 stuff all day long, but don't like losing control by group settings.
  • Conservative , believe in hardwork, planning for the future.
  • Want kids and a family. HUGE priority.
  • no mental problems, no family problems, no debt, no pets, nothing holding my down.

Past Relationships:

  • 5.5 years: she fat and lazy. 9/10 --> 4/10. Went from fun, brighten your day, helpful & making 125k to being lazy, and stereotypical woman working all day and thinking super important at 160k & 12hr days. She couldn't plan for future.
  • 6mo: 9/10. Blind to what went wrong. I wasn't born yesterday. Beyond normal relationship stuff, we had really deep conversations, she also believed in gender roles, conservative, talked about family, then out of blue with no fights and tons of fun, she told me after 6mo she didn't feel 'chemistry'.
  • A bunch of short term 1mo ones... I don't like to invest my time if don't see it going somewhere.