In the past year, I've gone from shy virgin to confident hookup guy. It seems like most people have gone through what I've gone through in HS/college but I'm learning as fast as I can.

To start, I'm not an overly attractive guy (5'4", boyish face, and basic level of fitness). When I've online dated in NYC (i.e. a place with a surplus of women), I still struggle to get matches on Tinder, CMB, Bumble, OKC, etc. It took me awhile to come to the realization that I wasn't super appealing physically, but it did change how I approached women. Initially I just did what (I think) a majority of guys do: tease, make some small-talk, joke about things happening around us, and sharing some common interests. After this realization though, I decided to really let my true personality come through on dates since my friends insisted that those traits (e.g. emotional depth, philosophical musings, and many historical anecdotes) are what they like about me.

My shift in dating conversation came with immediate results. Two dates invited me over after a few drinks and others said they couldn't wait for a second date. So this would be great, but I honestly haven't been able to reciprocate the strong feelings that they have for me. Instead of just not seeing them again, I feel like I'm not giving them a chance (it has always taken me awhile to warm up to anyone) and so we end up hanging out several more times. All end the same way though, women sobbing when they realize that I don't have this emotional connection back. In checking back with them later, it sounds like these extremely hurt feelings last for days.

I feel like I'm in a catch-22. On one hand, I want to play up my actual personality and want to give these women several chances to showcase theirs (3-4 weeks). That said, I feel like I'm leaving a trail of heartbreak and that these women would've been better off never knowing I existed. Two said that they hadn't felt like this about anyone in the past 3 years :/

What do other people do to avoid such lopsided emotional attachment and more importantly what can I do differently?

tl;dr: I don't know how to casually date and feel bad when my dates get so emotionally invested.