Dear Kiki: I’m twice my crush’s age. Do I have a chance in hell?

Questions about love and sex in the Iowa City-Cedar Rapids area can be submitted to, or anonymously using this form. Questions may be edited for clarity and length, and may appear either in print or online.

Illustration by Jav Ducker

Dear Kiki,

I am a single man; I’m 50 years old. I’m not a typical 50-year-old — I’m an artist, songwriter, performer and have always lived my life outside the mainstream. I’ve been married before and tried during that time to assimilate to a more expected life path. It was not a success. I need to live creatively, simply and not in service of making loads of money.

Anyhow, I have become friends over the past several months with a 25-year-old woman who has a similar disposition to me, has similar life goals and who I get along wonderfully with. I can tell I’m falling in love with her, but due to our age gap, I’ve been afraid to say anything to her. I can’t imagine a beautiful 25-year-old would want to be with a poor 50-year-old artist. I don’t know what to do. How do I even begin to tell her how I feel without embarrassing myself? Do I have a chance in hell?

—25 years too late

Dear Too Late,

You’re not. Insert standard platitudes about “love is not a number” and “the heart knows no age” and “you’re only as old as you feel” here. You know this stuff; you live in the 21st century. You fell for her because of your similar temperament, right, and not because of her youth—so why wouldn’t you consider her capable of the same?

What interests me far more, Too Late, is that you believe that you are “not a typical 50-year-old.” Let’s unpack that a little bit. Were you a typical 49-year-old? A typical 35-year-old? What do these terms mean to you? Were you a typical 25-year-old—and, more importantly, is she?

Because here’s the thing: 25 years is not a lot of time. If you think the similarities in your temperaments are due solely to age, what does that mean for 25 years from now? Do you expect her to be a “typical 50-year-old” then, and if so, will you seek out a new 25-year-old? Will you be a typical 75-year-old?

You may be atypical generally as a human being (and, frankly, kudos from me for attempting to live an anti-capitalist lifestyle in today’s society), but there is nothing about your age that circumscribes that.

Once you let go of this idea that there exists a “typical” that is defined by age, you may discover several things. You may discover that there are myriad people your age and older who also have similar temperaments to you. You may discover that the experience you have gained in life has value and is a selling point in any relationship, not something to be embarrassed about.

And you may discover the confidence to invite your friend into a deeper relationship.

Ultimately, age gaps only matter because of the increased potential for a power differential. So long as you are peers (you are not her boss, her mentor, her teacher), then you’re both adults, and (with hopefully unnecessary caveats about a willingness to accept “no” as an answer) you should give it a go. How many chances do you get in life to tell someone you care about how you feel? And after all, age is just a number.

If you’ll let it be.

Xoxo, Kiki

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