Sometimes when I write about past romantic experiences, I likely come across as more adept at romantic interaction than I think I am. So here’s a story about not getting it.
I was, for a while, on a dating site with religious overtones. Though I still wasn’t exactly devout, I was at the height of my religiosity. And hey, try something new, right? Well, I was on a meet-date with a nurse. Things were not going remarkably well when she tried to fill the silence with a hypothetical. What would I do if I won $220,000,000 in the lottery (that was the prize, getting a lot of headlines).
My first answer was that I don’t really do the lottery. Play along, she urged. Which I did. So I said that it would be hard to say without a spreadsheet handy and an idea of what the interest rates would be for regular payments on a long-term, low-risk investment would be. But it would probably involve setting aside a million dollars from the first annuity check (and I would definitely go that route rather than the all-at-once route) and then put the rest in some sort of low-risk investment account. At the end of the first year I would put howevermuch was required to get the account back up to a million dollars and then put the rest of the second annuity check in a similar investment. That way I could live off a maximum of a million dollars a year, but I would have growing principal that would lead to growing interest payments. At some point, I would probably switch it from one million to two. Or if I had an ambitious something-or-other I would have to consult a spreadsheet and determine a timeline so that I could have maximal investment while at the same time be able to do whatever it was I wanted to do.
She said that she would get a boat. And buy her mother a house.
The correct answer, if I’d actually understood the question, would have been the ambitious something-or-other I had in mind but was too embarrassed to come out and say.
“I would take some directing classes and make a movie.”
I don’t know if that answer would have come off better, but it would have at least answered the question that she was really asking. It would have given her some insight to my hopes and dreams and stuff. Of course, my answer gave her insight into two core aspects of my personality: I am practical, and I can be socially stupid.

When I was a child, we used to play a game called, “What would you do if you had a million dollars?” Oddly, investing never came up.
Actually, I really liked your answer. I think it effectively communicated something important about your character, and also effectively screened for partners you would likely want in an LTR.
But, okay, I guess the follow-up question would be, “what will you do with the income stream you have thus secured?” Then you can talk about filmmaking.
Comment by ? — March 28, 2011 @ 12:51 pm
My husband would have answered exactly the same as you did, god love him. We are talking about a guy who had six figures in his 401k by the age of 28, from a very ordinary salary.
Comment by Maria — March 28, 2011 @ 3:35 pm
Phi, a better answer would be to say something like “I would want to make sure I had a financial plan where I lived primarily off the interest, but I would spend the money on…”
It does act as a screen, I suppose. Clancy probably would have been impressed by the answer. Then again, she wouldn’t have asked the question. I think most people that would ask the question are looking for a boat or house answer.
Comment by trumwill — March 28, 2011 @ 4:12 pm
I said that it would be hard to say without a spreadsheet handy
There is no way this actually happened. No one is this retarded.
Comment by Mike Hunt — March 28, 2011 @ 6:13 pm
No one is this retarded.
You underestimate me, sir.
Comment by trumwill — March 28, 2011 @ 7:08 pm
“Two chicks at the same time.”
Comment by Kirk — March 29, 2011 @ 8:06 am
Wrong, Kirk!
440 chicks at the same time.
Comment by Brandon Berg — March 29, 2011 @ 9:44 am
Your answer in post 3 is MUCH better. There is nothing wrong with saying you want to invest most of it so you could live off of the interest if you had to. It shows responsibility.
The answer you originially gave is fine in a college class, if a professor asked you on a test how to optimize the winning of a lottery jackpot.
Finally, the question itself isn’t so bad. She wanted to know what your hopes, dreams, and ambitions are. Also, since there was a large jackpot in the news, she was discussing current events.
Since no one has asked, I will. How did she look? Was she a single mom?
Comment by Mike Hunt — March 29, 2011 @ 6:47 pm
Kirk, I wonder if I had actually seen that movie and that’s what made me think in Samir-like terms.
Comment by trumwill — March 29, 2011 @ 8:34 pm
Mike, I agree that the question is not so bad. I just didn’t understand the question.
She looked fine. A little thick in build, but not problematically so. Really nice smile. Not dumb, but sort of a pedestrian personality (the kind of woman whose future house will be furnished with copius amounts of wicker and Norman Rockewell-like pictures). Had fond memories of K-12, which is generally a negative indicator of romantic potential.
The dating site was not cheap, so it avoided some of the pitfalls of normal dating sites (though I think the “single mother” angle is overstated for the more typical ones, or at least was when I was on that circuit). Off the top of my head, I went on a date with two nurses, and Ivy-league educated school teacher, a local news TV producer, and a couple that I would have to think harder to remember.
Comment by trumwill — March 29, 2011 @ 8:41 pm
I went on a date with [an] Ivy-league educated school teacher
What was that like? Was she TFA, or did she grow up where you met her?
Once upon a time, when women could be teachers, nurses, secretaries, or nuns, the pool of potential teachers was of MUCH higher calibre than it is now. I’m sure it isn’t coincidence.
Comment by Mike Hunt — March 30, 2011 @ 8:58 pm
She was a standard teacher. She wanted to be one all of her life and being accepted into an Ivy League school didn’t change that.
She spent at least a part of her childhood in Colosse, though I can’t remember if it was part or all. When she graduated, she wanted to teach at a rural school somewhere, but found that rural life wasn’t for her. So she landed back in Colosse.
She was actually the only one I felt any sort of connection to that I met from that site. Turned out that I was wrong in thinking, at the time, that I was interested in something serious.
Comment by trumwill — March 30, 2011 @ 9:16 pm