8 Conversation Starters For Dates


Everyone can agree that the worst thing about first dates is the awkward silence that can come with getting to know someone new. While some people always have something to say to fill those quiet moments, most of us could use some guidance. Here are some fool-proof conversation starters that will get her talking – and help you get to know her better.

Conversation starters for dates #1

What’s your favorite film/book character?

This question gives you a great idea of what interests she has. For example, if she answers “Superwoman”, you know that chances are she’s into comics; but if she relates more to Carrie from Sex and the City, it’s fashion she loves. And perhaps sex. And the city.

Follow ups:
Any other preference questions will help you get to know her better: favorite time of day, favorite meal, favorite hang-out spot, etc.

Conversation starters for dates #2

How do you spend your Sundays?

One great way to get to know her is by finding out what she likes to do. If her idea of a good time is having a romantic picnic in the park and you love taking in a baseball game every Sunday, you’ll instantly know if there might be some trouble down the road.

Follow ups:
Describe your typical day.
What are your favorite hobbies?
What kind of food do you love?

Conversation starters for dates #3

What’s your dream city?

The answer to this can be very telling. If you both plan to travel around a lot, you may have more in common than you know. If she loves the city you both live in, chances are she’s here to stay. But if she reminisces about her hometown or dreams of moving to Paris, you know she’s got bigger plans ahead.

Follow ups:
Where did you grow up?
Where do you plan to settle down?

Conversation starters for dates #4

Tell me about your family.

Two topics to avoid on a first date: exes and anything too controversial, like politics. One topic that is very important: family. Knowing about a girl’s relationship with her family gives you an idea of what kinds of values she has, what sorts of relationships are important to her and what her history is like.

Follow ups:
Do you have any siblings?
Who are you closest with?

Conversation starters for dates #5

If you could retire tomorrow, what would you do?

This is a good question if you want to know how she would ideally spend her time. If she says she would love to open up a women’s shelter, you know she’s got a big heart. But if her answer is “shop all day”, you could be shelling out some serious dough in the future.

Follow ups:
Why is that important to you?
Where would you retire?

Conversation starters for dates #6

What was your best job ever?

The answer to this question gives you an idea of what her career life is like. If her only recollection results in “babysitting”, she may not be the most driven person. But if she loved her summer working as an English teacher in Spain, you know she’s adventurous and hard working.

Follow ups:
Would you do it again?
What was the best part?
What’s your career goal?

Conversation starters for dates #7

What’s the longest you’ve ever gone without sleep?

Quirky questions like this can bring up funny stories to bond over and give insight into her experiences and her character. If you both have outrageous vacation stories to share a laugh over, you know there’s chemistry there. But if your craziest moment was your prom night and she spent six months hitchhiking around Brazil, you may have less in common than you thought.

Follow ups:
More silly questions or a flirty joke (i.e. “let’s see how long we can go without sleep”)

Conversation starters for dates #8

If you could travel anywhere, where would you go?

This question may seem similar to number 3, but it will bring out different answers. If you both love travel and have a fascination with Australia, there may be a future there. But if she prefers to stay put and you’re into discovering new countries and cultures, this relationship won’t likely be long-term.

Follow ups:
What’s your ideal vacation?
Where have you travelled?
What’s your favorite country?

More conversation starters for dates

It’s always important to find common interests and activities if you aim to build a relationship in the future. One great way of doing that is by finding a partner using a dating site that matches applicants based on interests (you can read about two of these in this dating site comparison). Furthermore, these questions are designed to help you impress her with your conversation skills and figure out if she’s your type of lady.

So don’t be scared to ask away – and remember – a well-flowing conversation will lead to many more dates in the future.