27M here who hasn’t been in a relationship for almost 7 years. My father suddenly passed away when I was 20 and being an only child I had to quit school to take over his business. 5 of those years I went through a depressive rut where I didn’t have the fortitude to date. Just my luck when I began to feel better, Covid happened.

Due to my disinterest in the business and Covid’s hamper on profits, I cut my losses and sold the business. I’ve moved back home, reenrolled into my local state university, and I just finished my junior year. The funds I’ve accumulated from the sale and saving money at home help me study as a full time student.

In a recent class I’ve vibed with a classmate(30F) who is amazing and shares a somewhat similar story as myself(came back to school for new career). We’ve become somewhat close as friends, though not sure if my feelings are unrequited and she’s planning to go to law school after graduation(we both graduate next summer). I respect her decision if she’s not interested, and trying not to get too attached just in case she leaves far away after graduation.

Getting to the point, she made me realize that I have a desire to date again. However, I also realize I am a 27M who is a full time student currently living at home. The rational part of me knows it wouldn’t be fair to any women that already “have their life together”. Even though I technically owned/ran a business for 7 years, I’ve never actually had a career where I needed a degree and worked for someone else.

At the same time, I fear due to my late start, I’d have to wait until I’m 32 or 33 to date since it takes a few years to climb up from entry level and save up for my own place. I know that’s probably the smarter decision, just sucks to think I lost my entire 20’s decade haha.

I’m no supermodel, but I have been hit on a decent amount in real life. It also helps I have a youthful appearance since many of my fellow classmates think I’m 21 instead of 27. It’s just my anxiety of women finding out my late start personal circumstance.

Any advice or thoughts? Thanks

2 comments
  1. Everyone’s story is different! 🙂 There’s no early or on time or late & your current surroundings aren’t the entirety of the dating pool. There are great women/men who meet their future spouse in college/while one of them is at a different place in life. I’ve known several couples in which the woman used to be the breadwinner and eventually luck changed for the man and they are earning more/feeling more like a stereotypically good partner.

    Edit: Don’t be afraid to ask someone out, you have a lot to offer. Remind yourself of all your great features.

    Also, working for someone else does not make a job more legitimate than owning your own business. Just because it was your father’s, doesn’t mean you didn’t earn leading that company. Not having a degree doesn’t mean that your business experience wasn’t worth anything. You were dealt a pretty tough hand and seems you came out on top! Enjoy this time you’re getting to work on yourself. You’ve done great 🙂 Now you get to choose instead of having things thrown at you! Wishing you the best of luck! 🍀

  2. Ask your friend out on a date before she leaves. Dating isn’t just logic. If she’s into you, she won’t care so much about all the specific. And you are going somewhere in life. That matters more than were you are atm.

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