I’m (31M) about to do something stupid, and I need you guys to talk some sense into me before I make a massive mistake.
When I was in high school, I met a girl with whom I had an incredible connection. She was a freshman, and I was a junior. In the summer of 2009, we met through our mutual friend. We hung out and somehow found some alone time with each other. One thing led to the next, and we went from hugging to groping to aggressively making out, marking our first kiss.
That was the only time we met, and we parted ways until about two years later. We reconnected through a series of events and started hanging out more frequently as friends. We had so much in common: same ethnicity, interests, friends group, and a fierce desire for one another.
I eventually mustered up the courage to ask her out, and we began dating for about 2.5 years throughout her late high school years to sophomore year of college. Everything felt magical, but that’s probably because we were young and inexperienced. She lost her virginity to me, met each other’s parents, who eventually started referring to us as their in-laws, and even had dreams of potentially starting a family together when she was done with medical school.
She then moved away for college, about an hour away from home, and our communication plummeted. We went from spending every day and every night together to only on the weekends, and that eventually became every other weekend when she wasn’t busy with school or her sorority. I craved her attention and affection immensely, but she wasn’t able to fulfill my needs because her focus was on her academics.
Although everything felt right, I believe timing wasn’t on our side. She was heavily focused on school because she wanted to become a doctor, and I dropped out because I was working on building my travel company.
Our paths no longer aligned, and we began drifting further apart. I then made the decision to break up with her and decided I was going to live out my single life in my twenties, dove into the party life, and hooked up with a few girls. Although it was fun in the moment, when I reflect on my life choices it makes me cringe, regretful, and feel immensely upset.
We reconnected about a few months after our breakup. When she found out what I was up to, she was hurt but eventually forgave me, and we started dating again after a few months apart, only to end up breaking up again.
I admit, I was too immature and, like most guys, was unable to control my testosterone. We went our separate ways in 2014 and went no contact until 2021 when we were under lockdown. I added her socials, and she ended up following me back on FB and Instagram. Thinking we were good, I wrote an apology letter and sent it to her on FB during the loneliest and lowest point in my life. Honestly, that was the dumbest thing I ever did, and I deleted the interaction so I couldn’t tell if she actually read it or just ignored it.
Fast forward to 2023, I started to notice she may be stalking my Instagram because every time I posted something, she would post something a few days later. When I stopped, so did she, and the cycle repeated itself. That went on for the last year. I also noticed she was copying my hashtag formatting, but that could’ve been a coincidence.
It’s been almost 10 years since we’ve broken up, and for some reason, I can’t stop thinking about her. Over the years, I would think about her here and there and just forget about it, but recently it has become extremely common, to the point where I dream about her. I don’t believe in the psychological bs about “someone is thinking about you if you dream about them,” but recently I’ve had the urge to reach out and see if she’ll respond to a “Hey, I know it’s been a long time. I was wondering if you’d be open to grabbing coffee with me and catch up.”
A huge part of me is telling me not to do this because what could possibly come out of this? She obviously didn’t reach out to me over the years because I was the dumper, and because she spent her formative years in college, I’d imagine she had enough distractions to completely forget about me. After all, it’s been ten years.
However, another part of me wants to try and maybe have a chat with her and see how she’s doing. I don’t have any ulterior motives like trying to hook up with her again, but I’ve been having these thoughts that maybe we might’ve dated too young. The thought of me dating her again isn’t off the table. However, when I entertain this idea, I can’t help but think about what she was up to during the years. Did she have a bunch of hookups? Did she date someone after me? My mind is spinning right now, and it’s having a negative effect on my work throughout the day.
What do you think? Should I initiate contact or leave it as is?