Setups can be awkward.

Setups and awkward just go together. Even long before the official setting up takes place, there is a certain amount of awkward that takes place any time one of the setupee's gets brought up in conversation. And, since it seems to be the season to set Lindsey up with people (which I'm generally all for), there has been a fair amount of awkward floating around.

Before Christmas, a co-worker (who shall remain nameless) emailed me about some work related thing, but then mentioned in passing that she may bring her brother to the gala next year since he's such a great dancer...then proceeded to mention that he was single. This, of course, spawned a trail of emails about her brother between her and I, and frankly, by the end of it all he sounded pretty darn great. 

Today, she and I had a chance to catch up after the holidays, and we talked about all sorts of upcoming work things, and as she was heading out the door, I got up the guts to say, "So, what made you think to bring up your single brother to me in the first place?" "Well..." And then she proceeded to tell me all the great things about him (and he still sounded pretty great), but then she said, "But I'm afraid he's maybe too old for you." "How old?" "Well...40-some." "40-some? Or 40? There would be a pretty big difference for someone in their 20s." "I can't remember for sure...42 maybe?" Awkward pause. That would be, by far, the oldest guy I've ever gone out with. There's a good 15 years or maybe more between us....making him closer to my parents age than my own. It could be weird. It could be really weird. But it could be equally not so weird. I don't know. 

So, after some more talk of his life with several awkward pauses and no longer really looking each other in the eye so much, I asked a fairly critical question - was he even interested in being set up? She responded with an immediate yes, to which I asked, "By his sister?" Again, a pretty clear yes. I'm not sure I would put so much faith into my brother's set up choices, but maybe that's just me. 

After yet more awkward pausing...because really, at some point, what do you say in this type of situation? I wrapped up the whole awkward mess with, "Well, if it doesn't work, we all have a good laugh and move on, right?" I mean, I'd still have to work with the woman. "Right, right," she said as she moved closer to the door. But she left with full intention of making sure we met the next time he came to town. I hope he's into younger women.

So, after that fun little story, my question to my general viewing audience (parents excluded, as I already know exactly what you think of the situation), what do you think? Is 40-42 too old for me? Could we possibly have anything in common? Will it be weird? Am I too much of a kid at heart (or even just in reality) to date someone so much older than me? I am interested in hear opinions. 


Oh, a quick rundown of what I know about this 40-something mystery man: loves people, has worked for hospice, has MBA, currently has stable career, is a writer and has a background in theater, knows how to dance, is a great cook, has built homes in several Central/South American countries, has worked at summer camps for kids who have lost family members to cancer, has recently adopted a rescue dog, has never been married, has no kids, has "good hair"... Now, all I need to know is if he loves the Lord, attends church, doesn't smoke, and happens to like younger women.