I recommend volunteerism. People who give time to a good cause can be kind, grateful, and excited that someone wants to join them.

Also, volunteering keeps you busy. Strangers work together to stuff envelopes, lift boxes, organize snacks, or drive around. It’s easier to bond when you have to do something with someone else. 

At the end of a day of volunteering, your loved one will have talked to a bunch of new people. Even if he doesn’t trade phone numbers with anyone, he’ll have done a nice thing. It feels good.

Another idea? Skip the Small Talk, the event series, is built for this. People can use those parties to fine-tune their skills and look for friendship or love. I watched a Skip the Small Talk event in Back Bay and was impressed by how easy it was for people to chat. Organizers were also wonderful about helping people move on from conversations when they were done.

The other thing I’ll say is that even as a 50-something, you can be a wing woman for social time. If you have ticket to a show, bring him. If you’re going to a party, ask if he wants to attend. I learned a lot of social skills from older, confident people. If he’s missing that in his life, plan an activity or two. Yes, he needs peers, but all kinds of social activities help.

That reminds me … I went to school with someone who grew up in Florida around grandmas who socialized all day. She was always so good at hanging out and talking about everything because she had the energy of a of a retired person who was always ready to chill pool.

It’s nice to have companions of all ages. Instead of advising this young man on what to do next, maybe just hang out.

– Meredith