This essay started as a joke between friends and became an experimental essay that was rejected by editors. Why? You decide.
Being single at midlife is weird. Some people assume you must be coupled, and ask about your significant other (who?). Others treat it like an ailment, like there must be something wrong if you aren’t in a relationship. But sometimes people choose to be single, which is where I fall. After ending my last long term relationship, I just needed time to be alone. In fact, it was a feeling I felt so completely through me.
Across the world, the need to be alone — or at least to not focus on finding a relationship — seems to be a trend. Over the last year alone, there have been many articles about women opting out of dating, including an interesting overview in the Guardian and an insightful one on Capsule.
The Backstory:
This essay started as a joke between friends. I’ve been single for a few years after many years of relationships and two of my friends suggested maybe it was time to dip my toe back into the dating pool. They started pointing out men who they thought could be interesting for me. But I wasn’t interested. At some point, the discussion turned to my pickiness around men. So one afternoon, I wrote a list of qualities I wanted in a significant other as a tongue-in-cheek response. My friends insisted we go over the list over drinks, and that I write about it. So we did and I did.
The Essay
This Annotated List of Boyfriend Qualities Was Approved By My Friends
When he walked into our favorite cocktail establishment, my friends both pointed him out. It was a cold Maine winter Friday, and with his coat and jeans he wore cowboy boots and a cowboy hat. I immediately said I wasn’t interested.
“But he’s got a book! At a bar!” they insisted.
But the boots and cowboy hat alone aren’t turn-ons for me and I am no longer willing to settle for anything less than what I want.
At 44, I am single and good with it. Since I started dating at 15, I have had more relationships than I can comfortably count, including a marriage that lasted nearly a decade and nearly eight years in my last serious relationship. When that ended, I was devastated — even though I was the one who did the breaking up. For the last two years, I have dated a bit. There was even a man that I thought could be it, but things fell apart.
Don’t get me wrong: I’d love to fall in love again and for the last time. But I need more than fashion props now. Unless he’s emotionally available, interesting and attractive to me, I am not interested.
And yet, my friends are always keeping an eye out. That’s why one afternoon I started jotting down a list of all the things I want in a man and then I let my friends vet the list over cocktails.
Here is it, with some commentary from Melissa and Julia.
1. He’s got to be hot AND I have to be attracted to his specific hotness.
While Melissa and Julia may never understand why I didn’t immediately introduce myself to the cowboy, they totally understand that hotness is subjective. It’s essential that whomever I date is hot to me.
2. He’s got to be interesting. I want to be fascinated by him and love to hear him speak. But he also needs to be fascinated by me.
3. Reading is a must. Bonus points if he loves dystopian novels, crime stories, journalist memoirs and food writing as much as I do.
4. He has to like to go places and do things. Travel. Eat out. Try new places. Explore.
5. In case this wasn’t clear: must love travel.
These were easy yeses for my friends.
6. But he also needs to be a homebody. Going away is great. Coming home is the best.
Melissa and Julia were way less enthusiastic about this one, but agreed that if it’s important to me, it should be on the list. I guess not everyone dreams of curling up on the couch with their favorite fuzzy blanket and a book when they are away?
7. Must love beaches, the sun, swimming … dreaming of living by the beach is also a bonus. Must know what I mean when I say I just need to get to the water. Or when I want to dig my toes in the sand.
This led to a whole discussion about how Arctic-loving Julia said she’d like to go to the Bahamas with us. It was a boon, because Melissa and I LOVE warmth and beaches.
8. He has to be successful and have most of his shit together. No one has all of their shit together, and if they do, they have other problems.
Yes. Full stop.
9. He needs to have his own money.
“And lots of it!” Melissa quipped.
“Hell yeah,” Julia said.
I think they are into it. For me, this is about autonomy and power dynamics in a relationship. I want to be with someone who is on equal financial footing.
10. Must be understanding that I like to fill my time. I have a full-time job. I write. I teach. I blog. I take immersive vacations. I spend a lot of time with my kids. And I love to meet up with my girls. He has to understand that I will find time for our relationship in this craziness, but not expect me to give any of it up.
This was a yes, though Melissa and Julia paused a bit. Am I doing too much? Probably.
11. He can’t be a mama’s boy. He also can’t be estranged from his family. Happy medium, please.
This generated some discussion. I’m looking for someone with strong bonds, but not unhealthy ones. But they pointed out that sometimes estrangement is necessary. When is it okay to be estranged? What about serious ideological reasons? What about when the only family left has been given many chances and didn’t change?
We ultimately came to agreement that estrangement itself isn’t a deal breaker. But he needs to be willing to talk about it, and articulate why.
12. He needs to drink but not every night. I want someone I can go out with and have a cocktail or five without guilt or shame. If he wants to pour me a glass of wine after a long day, I am not saying no.
We toasted in agreement with this one.
13. Must love food. Must not be picky. It’s fine not to like some things, but I will not give up sushi, spicy foods, onions, garlic, so many veggies, pasta, rice, ramen or anything else I love for anyone.
As Melissa and Julia pointed out, this one isn’t really about eating everything. He can have preferences, same as I do. It’s about being okay with your partner eating what they desire without making it weird.
14. Must drive, have a car and enjoy driving. I would love to drive less.
My friends quickly zeroed in on this one. They were firm: He needs to be a good driver and enjoy driving. Car is optional.
“I guarantee that if you meet a hottie from New York, having a car won’t matter,” Melissa said with a lifted eyebrow. She’s right.
15. Must love my kids. Must want them around too.
16. Must like pets, especially cats and hypoallergenic dogs.
These are absolutely nonnegotiable.
17. Must like the outdoors but not insist that I need to backpack anywhere with him. Also, he can camp. I am happy for him if he does but I am not coming. Unless I want to.
“And I can’t see an instance in which I would want to,” Melissa laughed.
She’s probably right.
18. I sometimes change my mind on things unexpectedly. He must understand it’s okay to change your mind.
19. Must be supportive in all things.
20. Must understand when to back down.
Yes, yes and yes.
Oh, and cowboys need not apply.
The Rejections:
I only pitched this to three editors, and I received one actual rejection (two others just didn’t reply): “I don’t think I can use the boyfriend qualities one but first-person pieces as well as food and travel pieces do well.”
Ultimately, I went on to pitch that editor another essay and a food piece and she picked up both.
My Thoughts:
After this essay was completed, I pitched it to an editor I work with frequently, but it was a bit too experimental in form for her audience. I pitched to a couple of other publications, but ultimately decided to stop pitching this one. It’s fun and different, but I really wasn’t sure the right home existed for it right now because publications tend to write about midlife dating as something to be endured. At 40-something, I’ve been married and in long term relationships. I haven’t dated much for a few years because I needed time with myself to figure out what I really want. But that doesn’t mean when I start dating again, it needs to be a very serious thing or a super loose thing (seriously, as a midlife woman do I really have to be either looking for marriage or cougaring it out?).
So, this one was rejected. But I also decided that the right publication was ultimately my own.


