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7 Dating Would You Rather Questions, Including a Broke Heartthrob

Whenever dating comes up, someone always asks, "Okay, but what would you do?" Our app Infinite Balance has a whole theme built around that question, called "Swoon-Worthy Confessions." There are seven of them, from where you'd want to be asked out to a gorgeous guy with a mountain of debt. Here they are, with my answers.

1. The confession: in the group chat or out on the street?

Group chat confession vs public street confession question illustration

Both happen in front of an audience, which is what makes this one painful. I'd take the group chat. It's just as embarrassing with all your friends watching, but at least you can flip your phone face down and breathe for a minute.

I once walked past someone confessing with a bunch of balloons downtown. I'm pretty sure I turned redder than the person being asked. That day I decided the street was a hard no.

2. Spends big on you but is in debt, or never spends but is a millionaire?

Spends big on me but in debt vs never spends on me but a millionaire question illustration

At first I leaned toward the big spender. Someone who pays for everything on every date? Hard not to like that.

Then it hit me that all of it is borrowed money. I could picture us a few years in, paying off that debt together, so I switched to the millionaire. I can live with splitting the coffee.

3. Who would you last longer with: someone you love more, or someone who loves you more?

Someone I love more vs someone who loves me more question illustration

Bring this up over drinks and it'll eat the whole night. I'd pick the one I love more. When I'm only on the receiving end, I just feel guilty. I'm happier doing things for someone because I want to.

But when I ask around, way more of my friends pick the one who loves them more. If that's you, I'm honestly curious why. Is it just nicer to be the one who's loved, or did you once like someone more than they liked you and get worn out?

4. Hearing "I love you" every day, or a gift once a month?

Hearing I love you every day vs getting a gift once a month question illustration

"I love you" every day, for me. Gift day would be great, but the 29 days in between would drag.

When I told a friend, she shot back right away: "If you hear it every day, it's basically 'hi.'" I said I'd be fine with that. She still swore the gift was better, and then she paid for dinner. Actions over words, apparently.

5. Butterflies every day, or comfy like best friends?

Butterflies every single day vs comfy like best friends question illustration

Comfy. Give me someone I can see in a stretched-out T-shirt without either of us caring.

6. A gorgeous, actor-level guy with $1M in debt, or a plain-looking comedian worth $10M?

Super-hot actor with $1M in debt vs plain comedian worth $10M question illustration

Both of them only have eyes for you. One looks like he walked straight off a movie set but owes a million dollars. The other is a comedian with a pretty ordinary face and ten million in the bank.

I already picked the money back in question 2, so going for the heartthrob now would make me a hypocrite. I'm going with the comedian. Plus I'd probably laugh every day.

What about you? I'm sure some of you would look at that face and say a million in debt is totally doable.

7. A ripped but short boyfriend, or a 6-foot but super skinny one?

Ripped but short boyfriend vs 6-foot but super skinny boyfriend question illustration

Ripped. You're born with your height, but a body like that takes years in the gym. Sticking with something that long is attractive to me.

The friend I was playing with picked six feet and said "clothes just look different on a tall guy" about five times. Neither of us gave in, so we just moved on to the next question.


How many did you answer the same as me? Try it with your partner and you'll probably disagree on more than you expect. Infinite Balance gets a new theme every week. If you want to play along, grab it here.