I’m 18; he’s 31… but we are both Virgos. Can I start acting on my feelings for my boss?

Never mind the age gap, says our elder—think carefully about your work situation.

Dear EWC

Hi! I’m an 18-year-old senior in high school. I work at an ice rink and really love it! My boss is so cute and funny. We’re both Virgos and have so freakin’ much in common. The problem is he’s 31. I really don’t know what to do. We work together all the time and have hung out outside of work once. We talk about everything and have the most interesting conversations. Not to be cliché as heck, but I grew up pretty quickly due to family issues. But I’m at a great place in my life and very proud of who I’m becoming. I would say I’m very mature and most everyone in my life would agree (even my therapist!). I know he likes me back and it’s hard to resist. Venus is about to be in retrograde and that means love lives will be starting/changing/thriving. Please help. I don’t know anyone who’s been through this so I really would love some advice!

Good-Listener replies

You won’t be the first or last young woman who has a crush, flirtation, or more, with an older guy. In theory, you’re over 18, so legally neither of you is breaking any laws. I would simply proceed with caution. He’s your boss… and that alone can cause some tricky issues. That would be the case whether or not he is much older or your age. But, given the fact that he is your older boss, and you are an underling, there may be some problems—and depending on how management sees it, you could both, or one of you, lose your jobs. They may be afraid of legal problems. I would have no way of knowing since each company is different and I’m not an attorney. Just be aware of the possible complications.

Sometimes age really is just a number; sometimes it isn’t, depending on the expectations of each partner. He is 31, meaning he’s at a different stage in his life…  He’s had a chance to date, start a career, and maybe is ready to settle down. Are you ready for that yet? If you want to see him and have fun, that’s your choice. But I’d hate for you to give up school, or a chance to be young and experience the world by committing to a permanent monogamous relationship unless you are truly ready.  I don’t know how much life experience you have —perhaps a lot. Sometimes (I’m not saying this is the case) an older guy may take advantage of that… or may say one thing and you take it as another. Just keep things in perspective.

Again, I’m almost more concerned with the fact that this is a workplace issue. I’m sure he is a great guy and may truly be all the things you perceive him as. If you leave the job it will obviously be less complicated… just think before you act and I’m sure you’ll make the right decision. Good luck!

Letter #: 429689
Category: Dating/Relationship