Dear Annie: Is crush on younger coworker worth the risk?

Dear Annie: I have a crush on my 18-year-old co-worker, and I’m certain she one on me, too – even though I’m 42 and she doesn’t know my age yet. The age gap is too big, which makes me afraid to ask her out because I don’t want to ruin our friendship.

The last time I had a relationship with an age gap this big was with a 19-year-old woman when I was 33. Before that, I had a relationship with a 45-year-old woman when I was 25.

I’m not sure what to do. Transitioning our relationship from friendly co-workers to something possibly romantic is a huge step for me. But there’s a new movie coming out soon that I know she’s excited about, and it seems like the perfect chance to ask her out. But is it worth risking the friendship? And possibly complicating things at work? – Age-Gap Gambler

Dear Age-Gap: It’s important to remember that along with this woman’s young age comes a much different phase of life than the one you’re in. Your dating history makes you much more equipped than her to handle a relationship with such a significant age difference – and that’s assuming she is even interested in one.

A meaningful friendship can be just as, if not more, valuable than a romantic pursuit. It’s not impossible for this to eventually blossom into something more, but for now, I’d play it safe and focus on enjoying the friendship you two have built.

Dear Annie: I recently moved to Colorado to help out my daughter and her family. I’m a small-town woman, so living in the city with them was challenging, but I gave it a real try. I even sold my house and everything in it to make the move possible.

I am now back in my small town. After a while in Colorado, I struggled with the new lifestyle and ended up moving back. Now, I deeply regret leaving. I miss my daughter and her family so much, and the separation has been harder than expected.

How do I live with the regret of leaving? I asked my daughter if I could move back and live somewhere else, not with her again. She said no. What should I do? – Miserable in Vermont

Dear Miserable: Of course you miss your daughter and her family; after living under the same roof together, anything different must feel extremely isolating. On top of that, I imagine her reaction to you asking to move back didn’t help matters, either.

If relocating to Colorado isn’t in the cards right now, you’ll have to make do maintaining your relationship through phone calls, FaceTimes and visits, whenever you and your daughter feel ready for that step. Otherwise, see this as your chance to reclaim your small town as your home. This turning point is the perfect opportunity to fill the void you’re feeling with new friends and experiences in a place near and dear to your heart.

Send your questions for Annie Lane to dearannie@creators.com.