#Love & Sex

7 Questions to Ask on a First Date

by Rachel Weeks

7 Questions to Ask on a First Date

Congratulations! You found a special person and made it to the first date. You’ve picked your outfit. You’ve done your hair. You’re about to walk out the door when you realize you’re hitting the town with a near-stranger and have absolutely no idea what to talk about. Don’t panic: We checked with relationship experts for a few good questions to ask on a first date.


If you’re a nervous chatterbox like me, you spend first dates prattling on about one thing or another just to fill silence. Or maybe you’re just the opposite, and first dates make you forget your words entirely. Either way, it never hurts to come prepared with a few simple but revealing questions to ask on a first date.


Careful, though—a first date is a conversation not an interrogation, so don’t come overprepared. You shouldn’t need an arsenal of questions to get conversation flowing; if you do, maybe you don’t need a second date. Just bring a couple questions and come ready to listen. After all, you’re only responsible for 50 percent of the conversation.


To get you started, we asked relationship experts April Masini and Barbie Adler for a few questions to pose on a first date.




1. What do you do with your days?

Open-ended and casual, this question is great to start off the date. “Men love to talk about their work,” Masini says, “And most men define themselves by their work—especially single men.” It asks if your date has a job without assuming and allows them to go into as many or as few detail as they’d like.




2. What does your ideal Sunday look like?

This question reveals more about a person than you’d think. “If your Sunday usually consists of brunch followed by football for the duration of the day,” Adler says, “that may not be the best fit with a potential partner who wants to go to the gym for three hours with an afternoon filled with errands.”




3. Are you from around here?

“It’s a little provocative to give him the third degree on his folks, his siblings, his socioeconomic background,” Masini says. “This question is a polite way of asking him about his family history.” You’d be surprised how much you can find out about a person just by talking about his or her family.




4. What do you want to be when you grow up?

Adler was asked this question on a date, and she wholeheartedly approves: “This question was a really cute and fun way to inquire about a number of things, including what my ultimate goals were and where I wanted to be eventually in my career. In your 20s, this question comes from a playful place and conveys a lot of promise, a sense of hope, and a look at the future.”




5. Who was your role model growing up, and why?

“This is a great way to spark conversation, provide insight into your potential partner as a child, and learn more about past and present values,” Adler says. A person’s role model says a lot about who they are and who they want to be.




6. Do you date a lot?

“This is a way to find out if he’s a serial monogamist, just out of a long-term relationship or marriage—yes, 20-somethings are occasionally divorced—or someone who’s all about hanging out, playing the field, and not interested in commitments,” Masini says.




7. Do a speed pet peeve round.

For example: Toilet seat up or down? Dogs or cats? Night in or night out? Adler recommends asking about pet peeves because “It can indirectly give you a heads-up about times you two may be more like oil and water and less like spaghetti and meatballs.”




April Masini writes the critically acclaimed “Ask April” advice column and answers readers questions on the free Ask April advice forum.
Barbie Adler is the president and founder of Selective Search and a national expert on dating and relationships.