Just to give a brief backstory i’ve always been the overweight jonah hill/seth rogen jewish funny man. My crush “Emily” is a fit and active girl who’s amazingly charismatic. When she walks into a room anyone brightens up.

I had a good friend group from elementary to middle school before I changed my school and knew no one. Didnt party in highschool, barely hung out with anyone outside of school and if it was, it was just guys because I was terrified of talking to girls in any capacity. I’ve had a lot of regrets from that time frame in what I could have done different.

Once I started college I got a job at a restaurant and was making headways. Hanging out with coworkers and meeting their friends, getting invites to parties and things were looking up but my own insecurities were stopping me from ever making a move. Hell in my junior year after talking to a girl for more than three days straight I would go immediately to my female friends and ask their advice. They always gave me little tid bits of ideas and ways to execute but I was too scared.

In late 2022 things were still going the same. Good social life, making people laugh. The epitome of the good times, except for the fact i was still a coward when it came to ever making a move. Conversation was easy, but it’s always been a fear of messing up a friendship and rejection. Something i’m going to need to get over, especially if I intend to ever start a family lol.

Emily and I have been talking for about 4 weeks now. Usually over snapchat or instagram. Our work holiday party was a couple of weeks ago and I slow danced with her for two songs. Almost thought about leaning in, but that was a drunk thought.

Anyways i started to get a feel for her personality. She’s a dog lover, has a good major, and overall no screaming red flags aside from the fact she’s a partier like me. She called me on Friday asking to see a photo of my dog and how she volunteers at the local animal shelter. I asked for a link to apply and then she invited me to run with her the next morning. Yesterday she met my dog and we were getting along well and talked about making it a regular thing.

How would it be smart to go on from here? Do I continue to wait and not make it awkward? Or should I man up and invite her to do more things with me?

2 comments
  1. She has demonstrated interest, invite her to do something. Show you are interested as well, if you dont know howshe feels about you, do something mild like bowling or go to run again.

  2. You can try writing a letter expressing yourself or you can try texting her yknow but if she’s showing interest what’s the worst that can happen

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