Q—I wonder if you could give me your advice on something. I’ve been e-mailing a guy who I met through another friend online. We’ve exchanged about 4-5 emails, and I’ve found that we don’t have a lot in common. However, he is the perfect match for my sister, who would actually be interested in communicating with him. First, is it appropriate to tell him that my sister has similar interests and see if he would want to talk to her? If so, what would be a good way to approach it with him?
A—Saying it just the way you said it above would be perfect. As long as you act warm and respectful, you need to trust that he’s a man and, as such, is strong and competent. He can handle rejection. He will be fine. Furthermore, you are obviously telling him that you think a lot of him if you are willing to set him up with your sister. He may not take you up on your offer, but hopefully he will still feel your respect.