Popping the Question: What if I’m the One Who Got Away?


“Auntie Mai, why aren’t you married?”

Ugh. My 5-year-old nephew has apparently reached the age where bald curiosity meets peak candor, because he’s taken to asking me this question every time we see each other, as we did a few days ago. My response is always the same: “Honey, why do you want me to be married?”


More than once he’s said shyly, while hanging off my neck, “Because I don’t want you to be alone.”

Ouch. “Well, I’m not alone. I have you, and your sister, and Mommy and Daddy, and Grammy and Papa ... ”

“But I think you should get married,” he earnestly insists.

OK, enough philosophy; time to get real with this kid: “Well, what would I need to be married?”

At this point, he always screws up his adorable little face, as if I’ve asked him the meaning of life ... or whether he’s brushed his teeth yet.

“Hmm ... a husband?”

End of discussion, thank God.

Valentine’s Day can be an embarrassment of riches rich with embarrassment for single people, whether it’s a 5-year-old deeply concerned about you dying alone, or a well-meaning, happily married colleague who suggests that you do a story on the statistical undesirability of black, single women in online dating.


And no matter how much one’s version of alone differs from lonely, if I’m honest, it always stings, at least a little.

But then I think back to last Valentine’s Day, when I was a freelance creative trying to figure out my next big chess move. Only a week before, I’d moved back to my hometown after a 24-year absence—in part because the man I’d long been dating long-distance lived there.


But instead of feeling at home, I was sad, scared, set adrift, waiting for a sign, and starting to have the growing suspicion that my “boyfriend” liked me much better when we weren’t in the same area code. That suspicion would prove true months later, when an out-of-town friend spotted him on Tinder.

In short, I was lonely—far lonelier than I am now, when I’m basically married to my job (a concept I thought a bit too advanced for my nephew). But somewhere between trying to meet a man halfway and getting The Glow Up up and running, I went missing.


I’m not sure whether it was my constant attempts to be accommodating, the constant grind of trying to learn on my feet, or just the constant pressure to be all things all the time and never quite feeling that I was measuring up, but I allowed myself to get lost in the mix. I checked out, and I must admit, checking back in is harder than I thought.

And I know I’m not alone; every day I engage with the incredible growing community in The Glow Up Facebook group, and see myself reflected in the women there, all of us trying to stay present and connected—even when we’re not quite sure what to connect ourselves to anymore.


As I’ve matured, I’ve realized, as many of us do, that love is a choice; a choice we must make over and over again—sometimes in spite of everything else. But all too often, our concept of love remains fixed to factors that we have very little choice in at all, like waiting to get “chose” or finding someone “worthy” of choosing.

Why do we do that? Is it because it’s easier to throw our fates to the wind than to choose ourselves, even if no one else does?


I can’t currently claim loneliness; my life is too full of deadlines, and meetings, and personalities, and way too much stuff. I also don’t think about marriage much these days—there are lots of reasons I’m not married, and some of them are entirely on me. And, thankfully, I can say without bitterness that I don’t even miss my ex. When I think back on him and the men who preceded him, I feel no regret. (I don’t feel much of anything, to be honest.) There is no “one who got away.”

I also know firsthand what a difference a year can make.

But damn if I don’t miss myself. I gotta find that woman. And when I do, I’m gonna make sure she gets all her flowers.

Maiysha Kai is managing editor of The Glow Up, host of The Root Presents: It's Lit! podcast and Big Beauty Tuesdays, and your average Grammy-nominated goddess next door. May I borrow some sugar?



Another great read! You continue to be honest about these things with us, which makes you such a fascinating person. With all the gifts you possess: attractiveness, talent, intelligence etc., I am suspecting your ex must have been intimidated on some level. I remember being involved with someone ‘top-ranking’ - way above my level - and for a while wondering, why me? It was a huge ego-booster coupled with a sense of insecurity & intimidation. It lasted because she was a cool person! Maybe your ex, in his own way, couldn’t quite handle how blessed he was with you overall presence (package?).

“Damn if I don’t miss myself. I gotta find that woman. And when I do, i’m gonna make sure she gets all her flowers.” My gut says you’ve already got her; and here’s an additional bushel of flowers on this Valentine’s Day!