Hello Meredith-
I read your advice every day, and thought maybe you could help me.
Well, not really me, my brother. He lives across the country and is coming home for a few weeks during the holidays. I am excited to see him, but I also worry about him–he was recently let go of his first job since receiving his master’s, he has a tendency towards isolation and he has always had a difficult time meeting people. However, he is also a genius (literally), he has a fantastic, if kind of nerdy, sense of humor, he has all kinds of unusual and interesting hobbies, he’s skinny but very good looking and I happen to think he’s quite a catch for the right girl. He is kind, generous and respectful, and he is really a great conversationalist once he feels comfortable with someone. Plus he treats Mom and me like treasures, and we all know that a man treats the women in his life the same way he treats his mom and sister.
So you’re going to hate me, but I want to set him up.
I am not looking to set him up with his future wife. I just think it would be good for him to have some fun (platonically, unless they both decide otherwise) with some girl who is nice and treats him well, and it would be good if she was nice-looking also. I’m not too worried about the looks, though–my brother has this incredible ability to see the beauty in people, regardless of what others might see. He just has such a hard time meeting new people, and I want to show him that not every relationship he has needs to be serious. He’s had a few girlfriends (the first one had an “emotional affair” with someone else while dating him, the second was never actually attracted to him but dated him because she felt bad for him, and the third lived in an extremely conservative family who would not allow her to spend more than a couple of hours a week being social.) They were all good people but wrong for my brother. And anyway, I’m not looking for him to meet the love of his life, just someone to share his time with and have some fun with.
I guess the real question is, how do I set him up? How do I convince my (very few) single female friends that he is worth their time (which he is!!!)? How do I convince him to give dating a chance? He seems uninterested to the casual observer (like my husband, who tells me to stop worrying about it,) but I’m his sister and I know that he is lonely and wants to share his time with someone, but he’s too afraid to take the leap. How can I convince him that it’s sometimes just a numbers game, and eventually he will find someone to smile and laugh with? Most importantly, are there any readers out there who want a casual, low-key date with a nerdy but brilliant, skinny but Heath-Ledger looking, quiet but vibrant 24-year-old man?
It’s Christmastime and he’s lonely–throw me a bone here!

– Worried and Hopeful, New Hampshire