So last Tuesday I’m scrolling through Instagram when this ad pops up – some book called “101 Questions Before Marriage”. Normally I’d swipe past, but hey, me and Sarah are talking engagement rings soon. Figured maybe it’s worth a shot. Grabbed my keys, drove straight to Barnes & Noble. Found it shoved in the back of the relationships section, cover all dusty.

The Awkward Bookstore Moment
Paid at the counter – cashier gave me this knowing smirk like “good luck, buddy.” Felt my ears get hot. Threw it in a brown paper bag real quick. Got home, dumped it on the kitchen table where Sarah could see it. She picked it up, raised one eyebrow. “Seriously? We gonna do homework before getting hitched?” We both laughed, but underneath… yeah, nerves.
How We Actually Used This Thing
Didn’t just hand her the book like some professor. Made coffee Sunday morning – extra strong. Sat on the couch, knees touching. Cracked it open together, flipping pages randomly. Saw sections like “Kids & Parenting,” “Money Drama,” “Dealing with In-Laws.” Agreed: no pressure, just talk when something hits us.
- Started easy: “Where do you wanna live in 5 years?” Turns out she dreams of mountains, I’m a beach guy. Had no idea.
- Got real quick: “How many bank accounts?” She wants one joint, I wanted separate. We argued for 20 minutes.
- Threw curveballs: “What if one of us can’t have kids?” Silence. Then we actually talked adoption for once.
The Messy Truth About Tough Talks
Wasn’t all deep stares and hand-holding. Got heated about Christmas travel plans (her mom demands we visit every year, mine guilt-trips). Sarah snapped the book shut at one point. I slammed my mug down. Coffee stains on question #73 now. But after cooling off… we actually found a compromise: alternate years.
Highlighted parts that stung. Scribbled in the margins. Drew angry doodles next to the “debt” question ($16,000 in student loans she never mentioned?!). But writing down the arguments made us actually solve ‘em later.
Why This Actually Worked
The book’s just dumb questions on paper. What matters: forcing ourselves to sit down, pick one ugly topic at a time, and rip off the band-aid. No sugarcoating. Weirdly made us feel more secure. Seeing we could yell, then make up, then agree? That’s the marriage test right there.

Finished it yesterday. Cover’s bent, pages are coffee-stained, #89 about wills has tear marks. It’s wrecked. And honestly? Best $18 I ever spent.