Social quandary: Is it OK to accept gifts from an admirer?

He's always been a generous friend, but by accepting gifts is she leading him on?

Man in jeans with orange gift white background


Have you found yourself in an awkward situation? Has someone irked you and you’re not sure how best to proceed? If so, you’re not alone! Every week, we feature a reader-submitted quandary so that you can weigh in with your best advice. What would you do in their situation? If you’d like to submit your own quandary, click here.

I was in a relationship when I first met my friend *Dale, about 5 months ago. We hit it off right away because we have many of the same interests, which eventually led to us hanging out more — as just friends, of course. When Dale went travelling, we kept in touch over Facebook and we’d catch-up in person between his trips. He’d always come back with a thoughtful gift for me. For instance, he knew how much I like photography, so he brought back a coffee table book by a well-known European photographer.

When my boyfriend and I broke up, Dale and I started hanging out more. We’d go out to eat at restaurants or for drinks, but it’d often be at upscale places that Dale likes going to. Then he would insist on paying for me because I can’t afford it — and he can. The problem is that I’m fairly certain he has grown to have romantic feelings for me. He’s asked me to be his date for an upcoming wedding, he’s always showering me with thoughtful gifts, and he’s even offered to take me on a trip, all expenses paid. I enjoy his company immensely, but I don’t see him in a romantic way — and he knows that. He’s such a generous person, but I’m worried that some of that generosity may be his attempt to win me over. Am I being too sensitive…maybe he enjoys being generous? Or do you think that, in accepting these presents, I’m leading him on?

*Name has been changed.


Please comment below and help this reader with your feedback.

Read our previous social quandaries here.