Matchmaker Says: Just Don’t Ask

We asked our matchmakers: What questions should never be asked on a first date?

Two years ago we covered first date pet peeves — you know, those cringe-worthy behaviors we sometimes have to endure while sitting across from relative strangers. Since then, we have published first date guidebooks, talking-point lists, and even a first move tip-sheet.

Though, it wasn’t until Best Life reached out with a new question that we realized we were missing a big piece of the first date puzzle — that is, what topics we advise first daters not to surface.

So, we asked our matchmakers… 

What questions should never be asked on a first date?

Matchmaker, Sophy Singer, kicks off the discussion:

“So, how do you like (insert name of dating app/dating site/dating service) so far?” 

Everyone tends to want to discuss dating on a first date. Perhaps this is a theme because we naturally try to find commonality in conversation. Too bad! As easy as it is to go there, don’t do it!

This question launches the conversation into awkward places. Suddenly, one of you might start sounding like a crazy serial dater. On the other end of the spectrum, it may come out that this is your first date in ages. Either way, both parties start overthinking one another’s answers, which leads to judgement, which leads to miscommunication, which leads to…

You get the point. Just don’t go there!

Matchmaker, Remy Boyd, adds: 

“How many people have you had sex with?” 

Asking this question not only makes your date feel uncomfortable, it’s just plain ineffective — you can’t win no matter what the response. If someone is honest and discloses a low number, they might appear to be inexperienced. Whereas, a high number may express an inability to commit… or worse. The point is, no matter how you answer, it doesn’t serve either party. Stick to light questions. Ask about travel, good food, books, music, shared interests, etc.”

“How old are you?” 

I believe in the old adage, “age ain’t nothing but a number.” But, lots of people don’t! I recently had a client who rejected a date based solely on age, even though he checked all of the boxes on the rest of her list. To her, his age implied they were not at the same stage in life; i.e. he was immature and/or not ready for a long-term committed relationship.

Asking this question on the first date can lead to tense conversation where one or both parties feel like they must defend themselves due to age. Dates should be about having fun, not comparing driver’s licenses!

“What’s your credit score?”

This is a real no-no! If you ask your date his or her credit score, you are digging for information that is none of your business. There is a time and a place where finances should be discussed, but it is most certainly not on the first date. Ask this strange question and expect your date to flee!

Matchmaker, Dorothy Stover:

Past relationships.

No one enjoys premature probing into one’s romantic past. Speaking poorly about one’s ex, providing unnecessary details about past relationships (and breakups) is not advisable.

In fact, bringing up exes at all is not advisable.

I hear this complaint from clients often, and it is also often the reason said clients don’t want to go on a second date with the ex-inquirer. This can all be avoided by not asking about about exes, at all. Be cautious not to ask questions that may lead to the ex files, i.e. how long have you been divorced? Or… why are you still single? (and why anyone would ask the latter blows my mind!).

Matchmaker, Melissa Rogers, agrees with Dorothy on the last point:

“Why are you still single?”

What a disastrous question. Is it rhetorical, is it not?

The asking party might actually mean it in a sweet “you’re so great” kind of way, but the person answering has an incredibly awkward task ahead of them — trying to explain why they’re still single, even with the great career, fabulous friends, etc… It’s like trying to explain Stonehenge. No one gets it. The answer is most likely, “I have no idea why I’m single, because I want to be..?” And, where are you supposed to go from there?

Sophy Singer also echoes the importance of avoiding past relationships in date conversation:

“So, when was your last relationship?” 

What a super-meta/awkward question to ask on a date! Yes, we have all had past relationships. They are over now, which means that something went sour, right? Negative stuff. Sad feelings. Not my idea of keeping things fun and light! Laying out your (or your date’s) past relationship baggage on a first date is a sure-fire way to put out the spark!

Dorothy Stover continues…

“Do you want to get married and have kids?”  

All too often we focus on the future at inappropriate times. Before you begin investigating whether or not you have the same life goals, figure out if you actually want a future with this person. Do you like them? Do you feel like yourself around them? Do you have the foundation of friendship that could even lead to a happy marriage?

You might be wondering, when is it OK to ask about the future? 

Only if the topic comes up naturally or after the “we’re exclusive” conversation takes place. Don’t put your eggs in one basket until them. Date and date and date some more. If you’re dead-set on knowing the answer to these questions ahead of time, hire a matchmaker to ask the pre-screening questions for you.

But remember — wanting to get married and have kids in general doesn’t necessarily mean they want to get married and have kids with you. Also, just because someone says they don’t want to get married and have kids doesn’t mean they won’t someday (but, don’t bank on that hopeful change of heart). 

Family inquiry or status of parents marriage.

You have no idea what the “are your parents still married” question will unearth — so I recommend that you don’t ask it.

Yes, if things go well your family lives may well be intertwined. But the first date isn’t the right setting to broach the subject, as this can be a complicated topic for many — divorce, fighting with a sibling, family far away and on and on.  

Of course, if your date asks about your family, you don’t have to shy away if you’d like to share. Conversation often takes a life of its own and that’s OK. Just keep in mind that the purpose of a first date is to figure out if you want a second one, not if you want to marry or be in a long-term relationship.

In that vein, Matchmaker Melissa Rogers, offers another off-limits question:

“Do you go on a lot of first dates?” 

To be honest, if you’re just meeting someone, it’s none of your business how many first dates they go on. Or second dates. Or third dates. Your business is your connection. Instead, ask questions about their interests and hobbies or even what they’d order for their final meal on earth. These are the questions that will help you decide if there is a mutual attraction, and maybe even a second date of your own! 

Matchmaker, Coree Schmitz, makes an interesting closing point:

For me, the questions you should never ask on a first date are ones you don’t want the answers to right away anyway. Whether it be about family, politics, religion, marriage, kids, or something as benign as their favorite band – if you don’t want to know the answer, don’t ask it. You may not want to know the answer because of a personal bias, a previous relationship, or maybe because your ex plays in a popular band and you don’t want to know your date is a big fan. Whatever!

I don’t disregard that these topics will have to be covered eventually, but on the first date it’s important to remember that you are dating a person, not an agenda. By giving someone the chance to be more than your toughest questions, you might find more compassion for yourself and your date.

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