Dating older men? maybe…

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Minda,
What is your take on dating/sleeping with older men? When I was 21, I was dating a 35-year-old man. Today, I am 23 and I have started to see a 40-year-old man. The funny thing is that we have not revealed our ages to each other. It hasn’t come up in any of our conversations to date. We have gone on two dates, each ending with sex and morning coffee. A few months ago, I vowed to be single for a little bit since I was having too much fun not having to answer to a significant other. I am not thinking long-term with him, but I am really digging him!
What is a girl to do?
—Should I Take Him Seriously

Dear Should I,

First thought: No.

On second thought: I dunno.

You see I’ve never dated anyone significantly older than me. So, my immediate reaction was to tell you: no. And to tell you that this 40-something fella is probably no-good because, let’s be real, he has to know you’re practically half his age. I was going to tell you to stick to love interests in their 20s.

Then, I remembered a few things. Namely, all the age-appropriate dudes who I have dated. If I had had the good sense to ask somebody for advice on those men, I also would have been told no. They included:

My commitment-phobic, alcoholic, pot farmer neighbor.

The charming gent with the accent who never wanted to move past hand holding.

Those jobless, car-less, nearly homeless rappers (three of them).

But I didn’t ask anyone, and I dated those men (and many more). They weren’t any more gentle with my heart just because we happened to be born in the same decade. I spent months, if not years, regretting some of those relationship choices. Yet, on this side of 30 those mistakes don’t seem so serious.

I guess what I’m telling you is this: Don’t be scared. Twenty three is for making mistakes. It’s this messy, awful age when you learn you are not who you thought you were, the things you thought you wanted in life are not the things that will make you happy, and all the wonderful ways your life is going to unfold are not yet apparent.

Twenty three was the best-worst year of my life. I can barely look at my Facebook posts from 2008 without wondering who this woman was who felt things too deeply. It was the year, like you, I got free, but I was so blinded by heartbreak and uncertainty, I didn’t know how to enjoy that freedom. I had to learn a new way to be, and I did so by cutting my teeth on the wrong men.

My advice to you is to let yourself feel all the things you’re meant to feel at this age. Your words, “not having to answer to a significant other,” were said lightly at the end of your letter, but they hit me hard. I wonder if maybe you are eager to break your vow to yourself out of that same fear I felt of the uncertain, or whether you made that vow to ward off the uncertain.

The only way to defeat the fear of uncertainty is by clearing up some of the mystery between you and your middle-aged paramour. Surely, there is time between dates and sex and coffee for talking. Talk about your age. About how you like to be treated and about how you don’t. About the things you hold dear. About the trivialities in your day.

And then take a deep breath and tell him what you’ve essentially told me — that you’re feeling him, and that you’re afraid of being in a relationship with a partner who seeks to limit you, to confine you. You can be into an older man, without wanting to add a father figure to your life.

Then, you listen. It could be that he is looking for nothing more than what he’s given you on these past two dates. It could be that two dates are too few for him to know what he wants. It could be that he does date younger women because there’s a power dynamic that thrills him. Or maybe he feels that your youth is incidental. He has the answer to your question; you just have to be brave enough to ask him. As long as you’re taking your needs and your feelings seriously, you will not make the wrong choice about this man.

And, hey, if you do, that’s what being 23 is all about.

—Minda