Dear Prudence,
The struggles created by the pandemic have hit some of my neighbors quite hard (think serious illness, job loss, etc.). During these tough times, I’ve started bringing baked goods to all the neighbors in houses close to my own for most holidays throughout the year. I know it’s a tradition that is a little dated, but I’ve found that it’s a good way to be supportive in some small way without being intrusive. For background, I’m a single woman in my late twenties, and all my immediate neighbors have been either married couples, senior citizens, or other women living alone.
Recently, though, a single man about my age moved into the house directly across from me. On the one hand, bringing strangers cookies has become such an old-fashioned tradition that I’m afraid he’ll think I’m flirting with him in a fairly aggressive way if I just show up with a big basket of baked goods out of nowhere. I definitely don’t want to make him feel uncomfortable! On the other hand, if he becomes friendly with our other neighbors and realizes I bring everyone close by except for him baked goods for every holiday, I’m worried that could make him feel like he’s being intentionally snubbed in some hurtful way. Any tips on navigating this one?
— Caught in a Cookie Conundrum