In my work, I get daily emails from clients, friends, and acquaintances with any and all questions they have related to dating. This long question below is one I got not too long ago, and I wanted to share it with my GTJ readers since it also may have happened to some of us.
"I have my own personal question based on the whole dichotomous nature of online dating: What if you are fond of someone you met online, but only platonically? Is there any way, realistically, to transition that to a friendship? Also, here's a specific variation: Is it super rude to suggest that one of your OKCupid dates might be perfect for a friend? I actually think it's a really good idea because I like and respect my friends, and I share common values with them, but we have different tastes and like somewhat different guys. Moreover, I know this can work in practice because I have a friend who met her husband as a follow-up to his online date with her friend. However, I mentioned this option to a date last week, obviously in a nice way, and he got pretty offended. (And, btw, it was because we were wholly incompatible politically/ideologically, so it's not even like I said, 'Oh, I'm not feeling physical chemistry so why don't you try my friend, instead?') I thought I was making a perfectly reasonable suggestion, but apparently it may be a huge faux pas."
As for setting up dates that don't work out, I actually think it's wonderful, but I do have some caveats. If you think highly enough of someone to want to set him or her up with someone else, it's a huge compliment. That said, give it some time (at least a few weeks) before making this gesture. I would be offended if, on a date or even the next day, the guy said to me that he wanted to set me up with a friend. Even if I agreed that we weren't a good fit for each other (and I would only recommend doing this if it's agreed that there's a mutual mismatch, lest someone get upset), I'd rather have the suggestion come to me after some space/time. It's all about the timing and the framing of it.
I went out with someone once on two dates. After those dates, I concluded that, while he was very nice, he wasn't for me. (I have too strong of a personality for some people. If you know me at all, you know what I mean!) Anyway, when I kindly declined a third date, saying that I wasn't feeling the spark, he got defensive and said some things that I didn't appreciate. Again, you want to make sure to handle things nicely and maturely with everyone… especially with me since I have a big database of single people waiting to be set up!
For this simple reason, in addition to, you know, the possibility of love, it's important to make sure you're at your best on every date. Avoid being rude, having your cell phone out, drinking too much, talking about yourself the entire time, and generally being a poor sport about the date not going well. And, I look forward to the flak I'll take for this comment, but even if that date doesn't go well, for opposite sex couples, I still recommend that the gentleman pays. This way, he still comes off as generous, and he's showing that chivalry is not completely dead. And given that the first date should only be for coffee or a drink, it shouldn't break the bank.