The post 10 Questions Men Say They Wish Women Would Ask on a First Date first appeared on Crafting Your Home.
The server drops the menus, the small talk begins and within ten minutes both people have run the same checklist: job, neighborhood, siblings, last relationship. It sounds like conversation. It works more like screening.
Harvard Business School’s Alison Wood Brooks and her co-authors tried a different approach by studying speed dating. Daters who asked more questions, and particularly follow-up questions, were more likely to win a second date, according to their 2017 paper in the Journal of Personality and Social Psychology. Participants never saw it coming: people didn’t anticipate that asking questions would make them more likable.
Ten questions follow, built from large American surveys plus a few findings from psychology and history.
Ask what made him say yes, because men are more open to being asked than the script admits
In the fourth annual Singles in America study, 92% of single men said they were comfortable with a woman asking them out, according to Indiana University’s Justin Garcia, a scientific advisor to the survey of 5,329 adults.
A woman who makes the first move can follow with, “What made you say yes?” and get something rare: feedback on which part of her message landed. Most daters guess. The answer also gives him a moment to talk about himself without it sounding like a pitch.
Ask who he calls when a week goes badly, because friend counts have fallen fastest for men
Daniel Cox, who directs the Survey Center on American Life, found in a May 2021 survey that 15% of American men reported having no close friends, up from 3% in 1990. Among unmarried men not in a romantic relationship, roughly one in five said the same.
“Who do you call when a week goes sideways?” sounds casual and gets past job titles fast. A thoughtful answer shows whether a man has people in his corner or only plans on his calendar.
Ask how dating has felt lately, since nearly 7 in 10 singles sense a widening emotional gap
Match’s 2025 study, run with the Kinsey Institute among 5,001 singles aged 18 to 98, reported that nearly 7 in 10 respondents see a growing emotional divide between men and women. The release labeled the finding an emotional mismatch.
“What has dating felt like for you lately?” tests it in one sentence and invites a man to say something real about burnout or hope. Ask it flat, without the sympathy voice.
Related Post: Average Men Aren’t Getting Picked. Their Sex Lives Are Paying for It
Ask how he likes to handle the bill before the check arrives
Chapman University researcher David Frederick presented findings at the American Sociological Association’s 108th annual meeting showing that 44% of men said they would stop dating a woman who never offers to pay.
Women were conflicted: 57% said they offer to help, yet 39 percent hoped the man would say no.
Splitting the check is a values question wearing a billing costume. “How do you like to handle the bill on a first date?” costs nothing, and the numbers suggest both sides are keeping score privately.
Ask for his go-to order, because drinks buy time
Match’s sixth annual survey reported that cocktails on a first date raised second-date odds by 137%.
Correlation is not instruction, and the likelier explanation is lingering: a second round gives chemistry a chance to show up.
“What is your go-to order?” works for a margarita, an oat latte or a club soda with lime. It turns ordering into conversation instead of a transaction.
Ask whether he is a saver or a spender, since 96% of singles say alignment matters
Match’s 2022 study found that 96% of singles agree a partner with similar attitudes about debt and spending is important. First-date etiquette treats money as rude to raise, an odd gap given a number like that.
“Are you a saver or a spender?” gets the same information without sounding like a loan application. The honest answer reveals priorities faster than a résumé does.
Ask what he is looking for, and answer it yourself
Match’s eighth annual study found 69% of singles were looking for something serious.
Majorities do not announce themselves, which is how two people end up across the table from each other, both wanting commitment, both performing casual. “What are you looking for right now?” takes ten seconds. Waiting to find out takes weeks.
Ask about the thing he has wanted to do for years
The prompt comes from the question set psychologist Arthur Aron and colleagues used in a 1997 Stony Brook University study. Paired strangers spent 45 minutes trading increasingly personal questions and reported feeling closer than pairs stuck with small talk.
Writer Mandy Len Catron carried the set to a mass audience in a 2015 New York Times Modern Love essay.
“Is there something you have wanted to do for years and have not done?” gives a man permission to admit an unfinished ambition without defending it.
Ask what dinner looked like at his house growing up, because dating moved the table out of the home
Historian Beth Bailey’s book From Front Porch to Back Seat traces how courtship left the family parlor for restaurants and theaters, where the man’s money ran the evening.
The habit of treating him as provider has outlasted the parlor. “What was dinner like at your house growing up?” drags the conversation back to the home table: who cooked, who sat where, which dish never left the rotation. Ask a man about his grandmother’s Sunday cooking and the answer arrives fast.
Ask if he wants to see you again instead of waiting for him to decide
Match’s seventh annual survey, fielded in December 2016 among 5,509 singles, found that just 29% of women initiate the first kiss.
Bustle’s summary of the same survey described men as overwhelmingly in favor of women asking for their number. “Do you want to do this again?” puts the decision on the table while you’re both still sitting there.
Directness costs a little pride. Guessing costs three days of checking your phone.
Related Post: 8 Things That Make a Second Date More Likely, According to Research
Other Posts You May Like
- How Couples Meet Now vs. When Your Parents Dated, According to Stanford Research
- 50% of Gen Z Now Research Their Dates Before Meeting Them, Here’s What They’re Looking For
If you like what you just read, then subscribe to our newsletter and follow us on social media.
