At 36, I have never had what I would consider an official boyfriend. Then nine months ago, I met a kind, thoughtful, clever, creative, driven, stable, handsome, 6’3” (I know) man on a dating app.
I feel really good about Paul. So, naturally, I’m searching for any possible hole in this floating vessel of happiness so that I can either repair it, or get this over with by tearing it open, letting the water rush in and sinking it like every other ship I’ve ever sailed.
For that self-sabotaging reason, I was intrigued by a set of 250 questions to pore over with your partner that are designed to identify “red flags and non-negotiables,” according to Lindsay Roth in Romances & Practicalities. It’s technically a self-help book that aspires to assess compatibility and, ideally, fortify relationships.
Paul was enthusiastically in. (Did I mention he goes to therapy? Back off—he’s mine!) I didn’t want to assault him with all 250 questions straight away, although I will casually work them into conversation in the coming months. “Do you want to check out that new Thai restaurant? Also, would you help your friends financially if they needed it?” Here’s what we discovered over just a few conversations:
Do you have a vision for your dream wedding?
My boomer parents played fast and loose with money they didn’t always have, as did Paul’s. This has given us each a healthy fear of debt and a reluctance to spend on things like expensive cars and hypothetical weddings before we pay our credit card bills and max out our IRA contributions. So, we both agreed that, for us, Roth vs. Traditional is a far more important debate than DJ vs. live band.
What are your views on monogamy, infidelity, and polyamory?
As two over-therapized people with no problem analyzing the root causes of every emotion, we ended up having a very candid discussion about infidelity (bad!), relationships with colleagues (bad!) and backsliding with exes (happens to the best of us!). We also talked about threesomes. (That part wasn’t in the book, but it came up. It’s a hard maybe, okay? Don’t kink shame us!)
If we have children, who will change the diapers, heat the bottles, and so on?
You know what’s not sexy? Asking your boyfriend of less than a year if he plans to change the diapers of your hypothetical child. But I forge ahead, ready to sacrifice my relationship for the questionnaire. Paul may be a near saint, but walking my dog isn’t his favorite activity. He was saddled with the majority of pet care in his last relationship and fears regressing. That said, he says he feels differently about a human. I probably wouldn’t have made that distinction without asking such specific questions. Instead, my mind would’ve gone straight to, If he can’t walk a dog, how can I rely on this asshole to operate a Snoo?
How can we best support each other’s hobbies?
This man learned my favorite Taylor Swift song on guitar. Do you think I’d care if he plays Call of Duty four times a week? And I’m an L.A. girl who isn’t gluten OR dairy free. Do you think he cares if I fall asleep to Southern Charm?
How do you like to be tended to when you’re ill with something like the common cold?
The most important thing I learned from this one is that he isn’t too much of a baby when he’s sick. (Is there a bigger ick?)
So how did we do?
Listen, I realize that nine months in, I’m probably still in the “we’re so perfect for each other, nothing about him bothers me” stage. But thanks to Roth’s book, Paul and I now know that the vessel of our relationship is respectably seaworthy. Holes will undoubtedly appear, some easier to repair than others. But until then, land ho.
Abbey Caldwell is a Los Angeles–based TV writer
