Just a quick email to check in after your first date with Mark.
Another first date. How’s that working for you? But I should give you credit for trying, at almost 54, an age when most sane folks might figure out that a long-term relationship isn’t for them. You’ve had two, with some occasional short-term canoodling here and there, but the last extended relationship has already been over for nine years, so why in the name of Harvey Milk do you think that THIS guy is right for you?
OK, I get that you’re an optimistic guy. Maybe a kind of wishful thinking as we head into the new millennium in six months: hope springs eternal!
Here are some serious questions to consider:
Does it bother you that he’s a widower with three children, all living with him?
Do you care that he’s nine years younger than you are? Think about it. Like when you’re 75, he’ll only be 66. There’s a big difference between 75 and 66.
So what do you like about him, after ONE date? Here are some important considerations, based on what I’ve known about you as long as I’ve known you, which is forever: He’s got to be handsome because that’s you all over: superficial. I hope he likes classical music. Does he have a sense of humor? He’d better, but that’s all I’m going to say.
Is he politically liberal? You can’t bring him home to the family if he isn’t!
Does he complement you in some way? For example, you have no taste in clothes. Does he? If so, maybe you can wear his. How about manual skills? Does he manage the affairs of the house well? You’ve only ever rented apartments, so what’s the living arrangement going to be? You know nothing about, say, painting a room. Can you get up to speed and learn a few skills? OK, you can, but do you want to?
Does he like to read?
Look, see if he’ll go out with you a SECOND time, OK? If he will, just relax and don’t try to get too wound up and also just let him do most of the talking. You tend to try too hard. Find the rhythm. There always is one, you know.
And if you’re in doubt, try to imagine what Mom would have thought of him. If she would have liked him, then maybe this is the guy.
Your not-so-disinterested self in the future-