How to Approach Girl who Liked me in High School

Long story short, I (22M) am about to graduate college, but occasionally I keep thinking of this girl who really liked me in high school (for quite a while). I liked her too, but never expressed my feelings because I was shy, insecure and clueless. I didn't talk much, avoided eye contact, and when I did talk, it was awkward and at one point I said something really rude to her, which I never apologized for.

I feel bad for ignoring her despite her obvious attempts to connect with me, and while I never said "no", I regret not talking more to a person who put in a lot of effort to talk to me. I've had a lot of trouble with social skills since a little child, and growing up I wasn't very confident -- I got made fun of regularly, I had really strict parents, and I never learned how to fit in.

We are in different universities, and I don't use social media. Funny thing is, she recommended that I should start a social media account because "my account would be so fire" (as she said lol), but I never learned how to be popular, and I found it mentally draining (probably because I'm introverted), and eventually deleted them. I only have a Linkedin (for the sake of finding a job). I was thinking of sending a message via Linkedin (lol) and maybe say something along the lines of "Hi XYZ, hope you're doing well, it's been a long time since high school, if you are interested let's go out for a drink", and briefly apologize for my awkward behavior in high school (somehow).

Any thoughts on this? My feeling is that, well, better late than never, and might as well go for it despite it being pretty awkward.

​

Some pros about me:

  • I work out (my physique has dramatically improved since high school),
  • I have a good job lined up,
  • I'm pretty kind (I'm not the person to show off, I don't talk bad about others, I listen to others, etc).
  • I'm not the person to cheat (I'm not into hookups, I don't use social media, I don't flirt that often).
  • I cook my own food (by no means am I Gordon Ramsay, but I like eating my own food :)

Some cons:

  • I don't have any friends -- usually this doesn't bother me but once I think about dating and see how other girls have lots of friends, it gets into my head a bit.
  • I'm introverted and not very comfortable in large social settings (like parties) -- on the other hand, she's a lot more social, drinks a bit, better at small talk etc.
  • I don't smile that often -- some people that I have encountered told me that it looks like I'm pissed/really sad even though I'm not.
  • I don't have that many memorable moments -- I generally don't like thinking of the past, I guess my biggest accomplishment is that I went to a top 10 university in the US but I don't feel like bragging about that... outside of that I got made fun of at school, had awkward relationships with my parents, struggled with a competitive sport (that I really liked).

Areas that I will be improving on:

  • Dressing nicely -- didn't really happen in high school/college (partly due to strict parents, partly due to me not understanding). I do plan on putting more effort into my looks, haircuts etc. Smile a bit more often. Use cologne etc. Buy lots of new clothes that fit.


Submitted March 04, 2023 at 12:16AM

Long story short, I (22M) am about to graduate college, but occasionally I keep thinking of this girl who really liked me in high school (for quite a while). I liked her too, but never expressed my feelings because I was shy, insecure and clueless. I didn't talk much, avoided eye contact, and when I did talk, it was awkward and at one point I said something really rude to her, which I never apologized for.I feel bad for ignoring her despite her obvious attempts to connect with me, and while I never said "no", I regret not talking more to a person who put in a lot of effort to talk to me. I've had a lot of trouble with social skills since a little child, and growing up I wasn't very confident -- I got made fun of regularly, I had really strict parents, and I never learned how to fit in.We are in different universities, and I don't use social media. Funny thing is, she recommended that I should start a social media account because "my account would be so fire" (as she said lol), but I never learned how to be popular, and I found it mentally draining (probably because I'm introverted), and eventually deleted them. I only have a Linkedin (for the sake of finding a job). I was thinking of sending a message via Linkedin (lol) and maybe say something along the lines of "Hi XYZ, hope you're doing well, it's been a long time since high school, if you are interested let's go out for a drink", and briefly apologize for my awkward behavior in high school (somehow).Any thoughts on this? My feeling is that, well, better late than never, and might as well go for it despite it being pretty awkward.​Some pros about me:I work out (my physique has dramatically improved since high school),I have a good job lined up,I'm pretty kind (I'm not the person to show off, I don't talk bad about others, I listen to others, etc).I'm not the person to cheat (I'm not into hookups, I don't use social media, I don't flirt that often).I cook my own food (by no means am I Gordon Ramsay, but I like eating my own food :)Some cons:I don't have any friends -- usually this doesn't bother me but once I think about dating and see how other girls have lots of friends, it gets into my head a bit.I'm introverted and not very comfortable in large social settings (like parties) -- on the other hand, she's a lot more social, drinks a bit, better at small talk etc.I don't smile that often -- some people that I have encountered told me that it looks like I'm pissed/really sad even though I'm not.I don't have that many memorable moments -- I generally don't like thinking of the past, I guess my biggest accomplishment is that I went to a top 10 university in the US but I don't feel like bragging about that... outside of that I got made fun of at school, had awkward relationships with my parents, struggled with a competitive sport (that I really liked).Areas that I will be improving on:Dressing nicely -- didn't really happen in high school/college (partly due to strict parents, partly due to me not understanding). I do plan on putting more effort into my looks, haircuts etc. Smile a bit more often. Use cologne etc. Buy lots of new clothes that fit.
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