Dear Prudence,
A while ago, I took a second job. There I met Jessica, 15 years my junior; she was bubbly and charismatic and definitely one of those cool girls you want to be friends with. She went out of her way to include me and we became friendly. Cue the pandemic. We finished up work and all left the job. Jessica started her own business and wanted merch. I love helping people, especially with my art. But I always forget that mixing work with friendships ruins everything. Anyway, I designed her logo, and bought and painted a box of hoodies, knowing full well I might never get paid—and I haven’t.
In the meantime:
1) I made masks during the pandemic, got a bit in over my head (sold over 10,000), and had to figure out how to vertically integrate my family, neighbors, and friends into a “factory” to get them made. We got it all done, but it ruined my mental health.
2) I started IVF a year into COVID, and it made me feel insane. When it worked and I was pregnant, I was not a fun hang. When baby was born, I could barely function. Jessica hated babies and never wanted to be a mom, so I stayed away. I kept waiting and waiting to feel “normal” … my baby is almost 2.
3) I am a pandemic queer. With a lot of time for podcasts and no need to perform my gender, I realized I am non-binary. While working with Jessica, she would never use a non-binary coworker’s correct pronouns, even though my coworker didn’t seem to mind. Jessica’s excuse: All her non-binary friends were fine with not using “they” pronouns. Consequently, I wouldn’t really want to share this part of my life with her.
At first, Jessica would follow up with me to check in, but she eventually gave up. Well, it’s been 5-ish years now (I’m cringing). Every time I go into my closet, I see her box of custom hoodies and feel shame. I don’t care about getting paid, I’m just not sure if she even still has the business. Should I move on since there are enough compatibility issues? I’m not sure whether to trust my gut, because I get hermit-y, bad at maintaining friendships in general, and consequently don’t have many friends. But I can’t donate her merch knowing she might see someone wearing it someday and hate me (and I can’t destroy it). It feels like I already blew it. What should I do?