My little brother recently divorced his crazy wife. He’s 24 and he got married very young. He has three kids by his ex, and he’s never really had a chance to sow his wild oats, so to speak.
Since his divorce, he’s enlisted my help in finding him dates. He’s a little socially awkward, so he’s had trouble meeting women on his own. In the past few weeks, he’s developed a Facebook crush on one of my old roommates. He friended her and they’ve been talking, mostly just conversation through status updates.
The old roommate just got divorced as well, but she’s four years older than my brother. And I seriously doubt she’s into him like he’s into her. I suspect she’s only chatting with my brother to be nice. However, my brother has asked me to attempt to set up a date with the old roommate. I don’t have the heart to tell him she would likely find him way too dorky. Should I break the truth to him now? Or should I let him approach her on his own and see what happens?
— The Protective Sister
Your brother is a grown man. Part of sowing wild oats involves heartbreak, and if this little Facebook crush doesn’t work out, he’ll just have to move on. What happens (or doesn’t happen) between your old roommate and your bro is out of your control, so don’t waste your time fretting about it.
You mentioned that your brother is socially awkward. Socially awkward people have often led sheltered lives, surrounded by overly protective parents and siblings. The fact that you’re still trying to manage his love life tells me that you’ve probably always had a hand in his relationships. In order for your brother to develop social skills and meet people on his own, you’re going to have to let go.
As for your roommate, you might want to let her know that your brother is interested. That way, if she isn’t, she can stop leading him on. She might not realize that her simple Facebook conversations mean more to him than they do to her. Then again, maybe she is interested in him. If so, she can make the first move if you let her know what’s up.
Either your brother will be forced to move on or he won’t. Whatever the case, try to let the man live his own life. It’s fine to play matchmaker when a potential partner enters the picture, but then you have to stand back and let the chips fall where they may.
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