Expert reveals the WORST question you can ask on a first date – and it might surprise you
- A relationship expert has revealed the questions to avoid on a first date
- Devyn Simone, renowned dating coach, said you should NOT ask your date “why are you single?”
- Simone also revealed her other worst first date question and her top tips for finding a ‘great guy’
First dates can be tricky to navigate and you don’t want to start off on the wrong foot by asking a bad question — luckily a dating expert has revealed the WORST question to ask on a first date so you can avoid it and date like a professional.
Renowned dating coach Devyn Simone revealed how to master the art of the first date.
Simone, whose motto is ‘drink water and date someone who deserves you’, is an expert on dating.
Her expertise has been featured on The Today Show, Good Morning America, The Wendy Williams Show and most recently narrated Next her best tips for first dates.
The first question NOT to ask on a first date is “why are you single?” According to Simone, it’s a terrible question, even if your intention is good.
Renowned dating coach Devyn Simone revealed how to master the art of the first date. Simone, whose motto is ‘drink water and date someone who deserves you’, is an expert on dating

The first question NOT to ask on a first date is “why are you single?” According to Simone, it’s a terrible question, even if your intention is good
Simone says the problem with this question is that “you don’t necessarily get the information you’re looking for. And if you formulate it that way, you put (the other) in the background. You put someone in a defensive position.
People can be single for many reasons and life circumstances that they may not want to explain, and if they’re single because of a messy breakup, they probably don’t want to repeat that on a first date with someone new.
Simone suggested instead phrasing your question by asking, “What have you enjoyed about being single and what do you hope to find a partner for?” She thinks this question will help you understand if you’re both on the same page, without any awkward tension.
The next question the dating expert says to avoid at all costs is “How many dates have you been on since (insert app name here)?”
She said, ‘Don’t talk about that, no. If they don’t say anything, why? When they say 15, you wonder, “How many have there been this week?”
‘Connection starts with shared experiences. Part of that shared experience is that you’re both in the app. So ask about the activity, about the experience you are currently sharing.’
Simone also revealed her top tips on finding a great man for single women.
She said on the Wendy Williams Show: ‘Got your must-haves and deal-breakers. Three must-haves. Three deal breakers. Not a list of a thousand things, no one has a thousand things.”

The next question the dating expert says to avoid at all costs is “How many dates have you been on since (insert app name here)?”

Simone also revealed her top tips on finding a great man for single women. She said, “Got your must-haves and deal-breakers. Three must-haves. Three deal breakers. No list of 1000 things, no one has 1000 things’
Her next tip is: ‘make yourself available’. Think about the kind of man you want. If you want the kind of guy who works out regularly, be cute and go to the gym.
“If you like a man who likes sports, be cute and buy good tickets to a good sporting event. Don’t buy nosebleed seats, buy good mid-level seats. Why? Because you’re probably one of the few women out there, compared to the number of men out there.
“Put yourself in situations where you have the advantage.”
Her third top tip is simply: ‘eye contact, smile and fun to be with.’