5 conversation tips to avoid making a first date feel like a job interview
Instead of asking what they like to do for fun, try this instead.

Conversation tips to avoid making a date feel like a job interview.
Going on a first date with someone can be nerve-racking. You glean what you can from their dating profile and the message exchanges that help you feel secure in knowing you won't wind up on an episode of The First 48. But once you're in front of each other, the conversation reverts to surface-level chatting about favorite colors, foods, and hobbies.
What could've been a fantastic connection based on the person's Hinge profile turns into a job interview. By the time dessert comes it feels like you should be asking about salary expectations.
Carey Gaynes, a dating coach and relationship expert, shares five tips on how to avoid turning your first date into an interview:
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1. Skip the interview
"Let's not do that typical interview style of boring questions, where it feels more like somebody is sitting...with a checklist going, they went to school, they majored in something I think is practical," Gaynes says in a YouTube video. "Skip the interview, there's other ways to have conversations on a first date."
2. Ask open-ended questions
Gaynes recommends asking open-ended questions that you'd be curious to know the answers to, whether you see them again or not. This means not just asking things that require a yes or no answer, and not asking questions that would only need a short response, such as, "Where do you work?"
While it can be great to know what a person does for a living, asking where they work is likely not going to tell you much outside of whose name is on the building.
Couple enjoying a cozy evening with wine.Photo credit: Canva
3. Ask questions that will open the conversation faucet
"'You said in your dating profile that you love traveling. Do you have any suggestions on where I should go on my next international trip?'" Gaynes suggests. "'Or any places you've been that I should avoid because you have a crazy horror story? In fact, share your horror story with me.' I love to hear about vacations gone wrong. I mean, there's some humor, and it's silly, but at least you're not getting, 'I have two older brothers, we're three years apart, except my sister's five years younger.'"
Gaynes emphasizes that if you've asked a question you consider to be good or noteworthy, ask a follow-up question if the answer given is short.
She explains that if a date reveals that they just changed jobs during the conversation, appropriate follow-up questions would be, "what is the job that you got? Is it in the same field? What made you pick that? Were you looking for that job, or how did you come upon it? Do you work from home? Do you have to go into the office? How are the people you work with?"
Romantic evening with laughter and bubbly on the balcony. 🥂✨Photo credit: Canva
4. Ask for the story you want to hear
Often, when dating someone new, you want to hear stories about their life. Typically, they come through lengthy conversations, sometimes several weeks into dating. Gaynes points out that you don't have to wait for it to come up naturally—simply ask for the story you want to hear. Most people love talking about themselves, so just ask.
You can ask for a story about how they decided on the job sector, or for them to tell you their favorite part of a neighborhood. Is there a time in their life when they felt most adventurous? Then follow up by asking if there's one thing they did during that time they'd like to relive. Getting a little creative with the questions can help you figure out if you're likely to have a connection through a mutual experience.
Enjoying a heartfelt conversation over lunch.Photo credit: Canva
5. Instead of focusing on a good first date, focus on a good conversation
It seems as if all of the tips Gaynes shares lead to removing the pressure of expectation from the person you're going on a date with. Instead, focus on having a conversation you want to be a part of.
There's nothing more frustrating and disappointing than a dry conversation or sitting in silence while you both pick at your food, racking your brain for something the other person might want to talk about. Forget that unrealistic pressure. Bring up topics you want to know about or raise questions you wish the other person would ask you. Ask for the story you want to hear.