5 First Date Questions to Avoid (And a Few Alternatives)

There are certain questions that are a big No-No when it comes to first dates. And clients share them with me. All the time. For 27 years as a dating coach I’ve heard them all, but this week I got an earful. 

And I work with intelligent people. Successful. But often the questions they ask on first dates leave me flabbergasted.

Maybe there’s something in the air this week. Summer is right around the corner, and this is a super busy time to date. And I’ve been super busy too which increased the number of phone calls with clients, reviews of texts with potential dates… and, well, date conversations.

Then, you wonder why there’s no second date. Men. Women. I work with both sexes – and they both do it!

Let’s dissect those questions, shall we?

Question #1: “How Long Have You Been on the Dating Apps?”

Why it’s problematic: It implies judgment and makes the date feel like a seasoned “dater,” potentially creating discomfort or defensiveness.

Who cares? Why would you care? Especially on a first date. How on earth does this affect whether you go on a second or third date or marry him/her?

I have so many examples but I’ll go with this one: Lara (not her real name), 61. Spunky, funny, athletic and pretty. We are looking through men’s online profiles together (by phone), and by the 4th time I’ve picked a high potential date for her, she says the same thing for the 4th time, “No, I’ve seen him online for the past 6 years. He’s a player.”

Ok, I’m direct. Very direct – but graciously so – as my only interest is for my clients to succeed in finding a long-term relationship.

Me: “Lara, and you know he’s a player how? And you’ve been online how long?’

Lara: “That’s different. I’m picky.”

Me: “I bet he is, too. I read his profile. He seems lovely. I want you to give him a try, and by next week, when we have our coaching call, I can’t wait to hear about your date.”

Reluctantly, she did. Reached out. Date scheduled. Turned out he was an interesting and kind man. He’d been traveling quite a bit with work and getting three kids settled in colleges, graduate school and internships as a single dad for the last 4 years with not much time to look at his online dating app. He told Lara he was grateful she’d reached out. Fingers crossed Date 2 goes as well.

Question #2: “How Do You Like Match, Bumble, Silver Singles, Etc. (Whatever App They Are On) So far?”

Why it’s problematic: It shifts the focus to the app rather than the person, often leading to negative rants.

Nobody likes a Dating App until they meet someone… then it becomes the greatest site in the world.

Question #3: “What Are You Looking for?”

Why it’s problematic: It’s too direct and makes the date feel like a job interview, putting unnecessary pressure on them.

If you are unlucky and get this question, cut it off quickly with this: “A second date with someone I like.”  Then change the topic and move on to getting to know each other – books, film, music, activities, current events.

Question #4: “Why Did Your Last Relationship End? Do You Have a Good Relationship with Your Ex?”

Why it’s problematic: It’s too personal and can bring up negative emotions or stories, which is not conducive to a positive first-date atmosphere.

After all, a first date is nothing more than a precursor to a second date, then hopefully a third date… and so on and so on. Yes, it will come up, naturally and in time, but this is not the time.

Question #5: “Tell Me About Yourself….”

Why it’s problematic: I know this isn’t really a question, but it’s in the same category. Also, it’s vague and can make the date feel awkward; like they need to deliver a monologue or résumé.

By the way, a client of mine got this question and she began with: “I was born at 6:04 PM on Tuesday, May 9, 1961 at St. Luke’s Hospital in Philadelphia…. Shall I go on?”

Her date started laughing and said, “Sorry, that was a stupid question.” The date went well after that. Ice broken.

Suggested Better Questions

If you don’t know how to break the ice or are a bit shy, here are some better alternatives to try.

Question #1: “You Had Great Photos – Where Did You Take the Scuba-Diving One?”

Why it’s good: It shows interest in their hobbies and experiences, leading to a potentially engaging story.

Question #2: “Where Are You From?”

Why it’s good: It’s a simple, open-ended question that can lead to discussions about background, culture, and upbringing.

Question #3: “What’s the Best Concert You’ve Gone to? Favorite Films? Books?”

Why it’s good: These questions delve into personal interests and can reveal shared passions, making the conversation more lively and enjoyable.

Additional Tips

Keep It Light and Fun

The goal of the first date is to enjoy each other’s company and see if there’s chemistry/connection.

Active Listening

Show genuine interest in their responses rather than planning your next question.

Shared Experiences

Discussing activities, music, or books can lead to discovering mutual interests, which is great for building a connection.

By focusing on these types of questions, you and your dates can promote a more positive, engaging, and enjoyable first-date experience. And, hopefully, a second date and more!

Let’s Have a Conversation:

What do you write in an initial message to a potential date? Is it unique? What do you talk about on first dates? Are you sending many messages out and receiving no response?