I am a 27 year old male who has never been on a date due to a variety of reasons – strict family, anxiety/depression, lack of confidence, height (I’m only 5’2”), etc. I’ve never even kissed a girl or anything. I am moving to a big city (think Philly, Boston, Chicago) for the summer for an MBA internship and figure it might be the perfect time to start trying to date and see how it goes.

I would appreciate any advice you can give!

A bit more about me:
– 27 years old guy
– 5’2” height
– In decent shape – not muscular/fit, not overweight, just average/a little skinny
– Well-educated (think professional degree like PharmD/MD/DDS plus MBA) and have good income potential
– Well-traveled and generally pretty knowledgeable about a lot of things but not really into sports
– I would consider myself an extroverted introvert (I enjoy talking to people and meeting new people but also need time to myself. I am on the quieter side especially with new people or in big groups. I am not great at talking to new people.. especially girls. I am much more social in groups smaller groups of 2-5 people and when i’m with people I’m comfortable with. Not really a fan of big parties or huge events but love smaller parties within a friend group or smaller get togethers. I have a decent amount of friends – a large portion of whom are girls and in hindsight, I’m fairly certain at least a couple of them have liked me in the past but too late now as they’re all in serious relationships)

I don’t really know what I’m looking for but would appreciate any advice or insights or tips you can provide!

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