21 Questions to Ask Yourself About Your Boyfriend
Twenty one questions to help you get at the heart of it.
There is a very old genre of women's magazine writing that promises to tell you if he’s the one based on a simple set of yes or no questions. Does he open doors? Does he text back within four hours? Is he at least 6 feet tall? Tally your score at the bottom to find out if it’s meant to be.
And it’s not that these lines of inquiry are wrong, exactly. It’s just that they’re a bit formulaic, and they don’t really capture the heart of what it means to love and be loved.
The answer to whether or not he’s right for you can’t be captured in a simple checklist. But it can be found by getting really honest with yourself — and that’s exactly what these questions are meant to help you do. More than any specific answer, listen for how each question makes you feel (and which questions you want to skip).
21 questions to ask yourself about your boyfriend:
How does he treat you when you’re on your period?
How does he treat you on your birthday?
How do you feel when you smell his sweat?
If you had a daughter, how would you feel about her dating someone exactly like him?
If a true emergency happened, how would you feel about him being your emergency contact?
Does he engage when you tell him your dreams or desires?
When was the last time you were silly or playful around him? How did he respond?
Is he curious about you?
If you woke up tomorrow with zero ties to each other (no shared lease, no history, etc) would you choose the relationship again, from scratch?
What does he do to make your life easier?
How have you improved since you met him?
Is he kind enough to push you out of your comfort zone, while also helping you feel safe enough to do so?
How does he approach issues that affect people that have little or nothing to do with him?
Does he genuinely enjoy giving you pleasure (both in sex and in spending time together), just for the sake of your pleasure?
What would your fifteen-year-old self think of him?
Has he taken the time to learn your body?
When is the last time he changed your mind about something? What was it?
What was the last book he read? Who wrote it?
How does he act when he doesn’t know the answer to something?
When something good happens, is he the first person you want to tell? What happens after you do?
If a friend described this exact relationship to you, in every detail, what would you tell her?

