10 Hilarious and Unexpected Questions to Ask on a First Date

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First dates are exciting, awkward, exciting, fun, horrible and just plain hilarious. Hopefully they’re more exciting and fun than anything else, but those of us not dating do love to hear about your hilarious and awkward and awful first dates. It reminds us why we are happy to be married and have kids and not have to go on any first dates ever again. But in all honesty, I haven’t been on a first date since I was 18 and that barely counts as a date because we had no idea we were going on a date. I was asked to dinner by friends who picked me up and surprised both of us by introducing us, which was a total date setup. They’d been trying for a while to get us together, but we’d never seen photos of one another and no one was interested. So, we chose not to meet. It’s been 14 years, 10 married, four kids, two houses and a lot of love and laughter since that night(we had dinner, went to the driving range and even went bowling…we ended up trying to make that night last forever, I promise). So I probably do not get a say on first dates.

With that said, first dates are filled with questions. It’s how you get to know one another, by asking thoughtful and interesting questions that provide a way for the other person to open up. Since I have no idea what a first date is like (and barely remember), I thought it might be fun to come up with a list of hilarious and unexpected first date questions to ask from the perspective of a couple that’s been married for 10 years.

What would you say if we had two kids and then found out number three was actually twins?

It might sound off the wall, but sometimes these are the questions you need to know. I mean, 8 years of marriage, two little girls and what we were hoping was a little boy turned into another girl and a little boy at our 18-week ultrasound. It would have been nice to maybe have talked about what would happen in a situation like that in advance. You know?

How often do you think you will tell me our kids are “MY” kids because of their behavior?

What you’re looking for here is, “All the time,” because you want an honest spouse. If you ask this and someone says, “Never!” they’re liars and you need to move on. “Our” kids become “your” kids with every annoying behavior. It’s what good marriages are made of.

Are you going to take it out on me when my mom makes a copy of our house key and lets herself in whenever she wants?

Again, the answer is yes. Because you want someone who is not going to just be a you-know-what to your mom and force you to keep the peace. But you should follow that up with, “We will immediately change the locks and never ask her to check on our cat again. If it doesn’t make it through vacation, we’ll get another,” or she might leave you.

Are you going to let yourself go after kids, or stay looking good?

It’s important. I told my husband right away that I had no intentions on letting myself go after kids. I’m too vain for that. He, on the other hand, didn’t mention he’d be the one eating for two when I was pregnant three times. Thankfully, he also goes back to normal when the kids are all born.

Do you cook well all the time or just a dish or two and that’s what I’ll be forced to eat all the time?

If there is one question my husband wishes he would have thought to ask, it’s this one. He really, really, really wishes he’d known this. I mean, really. He had no idea he was marrying someone who could only cook like three dishes and nothing else. It’s a good thing that he’s a good cook and I’m a good picker-upper or we’d be so hungry.

Do you love backhanded compliments?

Gentlemen; ask this one. You need a woman who doesn’t mind them because you guys are full of them. “I love that dress on you, honey. I wish you looked this good all the time,” and “Thank you for making dinner. It was delicious. Maybe next time you could hold off on the blue cheese, though. It was a little blue-cheesy,” are not really all that nice.

Are you a good list-maker?

What he’s asking is whether or not you’re going to make him listen to you when you need something or if you’re just going to write it down. It’s his way of letting you know that you should become a great list maker since it’s the only way you’re going to get everything you asked for the first time you asked for it, and it’s the best way to prevent an argument.

How do you feel about killing bugs?

If he’s asking, it’s because he’s not a fan of killing bugs. If you’re asking, it’s because you need him to kill the bugs. Do what we did; hire pest control and let them kill the bugs. No price is too high.

Are you more the good cop or the bad cop?

One of you has to be the bad cop, and it’s not always fun when you have kids. So you should ask this question since you need to know if you’re going to be the least favorite parent before you make the decision to have kids.

Do you like to drink?

Perhaps he’s just a wine aficionado and wants to take you wine-tasting across the world. Or perhaps he is asking because he knows that his family is totally crazy and it’s the only way to get through holidays. Either way, if he’s asking, you better learn to like to drink or move on from that one.

Photo by Chris Hondros/Getty Images

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