So, last month I matched my half-brother (19) with a friend of mine (24) who was interested.
I introduced them, schooled my brother a bit, supervised their first dates at my father's home and around town from a distance, and then left them to their own devices. Nevertheless my brother keeps spamming me with texts and calls asking about this and that; while talking with the girl she noted that sometimes he was withdrawn and that she needs to give him a little push at times - but overall she's happy with him. Finally, she told me that he's still a bit shy, and at that point I told her bluntly that since she's experienced and he isn't, to take the initiative herself and "seal the deal" this weekend.
I've also made it clear that this is the last time I get involved, because it's not exactly normal for me to have to dictate all their interactions.
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