10 Fail-Safe First Date Conversations

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I brown out on first dates. It’s kind of like blacking out (minus alcohol being involved), but rather than forgetting the whole date, my brain seems to switch off at certain points and I forget whole chunks of the conversation. I always thought it was those first date nerves, but thinking back on it, I now realize it’s because the conversation was duller than watching paint dry. A first date conversation should be lively, it should be interesting, and at the bare minimum, it shouldn’t make you want to take a nap.

If you’ve been out on your fair share of first dates like me, chances are you’ve gone on one where the first date conversation was seriously lacking. On these types of dates, the conversation seems to revolve around your meal, like:

“How’s your salad?”
“It’s really good, how’s yours?”
“Yeah mine’s good too”

Followed by more awkward silence. It looks like the conversation (and the date) are going south fast. If you find yourself in this situation and are struggling to keep the conversation flowing, then remember these 10 fail-safe first date questions so you don’t “brown out” like me.

1. What’s the most adventurous thing you’ve ever done?
This is usually a great way to start a conversation, unless he responds with something totally unadventurous that he thinks counts as adventure like “one time I stayed out past curfew when I was 16” …yawn. Let’s hope he has a story about something slightly more adventurous than that!

2.  If you could travel anywhere in the world, where would you go?
This is not only a good conversation starter, but it also opens the door to a whole new world of topics. If he wants to go to Australia, you can talk about everything you know about Australia, like kangaroos and shrimp on the barbie.. Or at the very least give him your best Aussie accent. And by best, I mean your awful impersonation that sounds more like a mixture between Borat and an old British lady.
3.   What’s on your bucket list?
Everyone has a bucket list, whether they consciously think about it or not. This is an easy way to see what his greatest dreams are without directly asking him and putting him on the spot. If he says skydiving, it shows he’s adventurous. If he says start his own company, it shows he has goals. If he says volunteer in a third-world country, it shows he’s selfless. The items on a person’s bucket list can tell you a lot about them if you pay close attention.
4.   What were you like as a child?
It’s always fun to share stories from your childhood, and it’s a good way to keep the conversation light and fun. Hearing about that time he got pantsed at the school assembly might still be traumatizing for him to think back on, but it’s a hilarious first date story to share.
5.   What are you most passionate about?
If all other conversations fail, this should always be your go-to question. If a person has passions, they are usually able to talk about them forever. For example, if a guy were to ask me about animals, then that’s almost guaranteed to be the only thing i’d talk about for the rest of the date: Like how cute puppies are. Has he seen that Husky in the bath video? What does he think it would it be like to talk to animals? Why are giraffe’s necks so long? See what I mean… endless conversation!
6.   How do you like to spend your weekends?
How a person spends their free time gives you valuable insight into who they are as a person. Does he spend time with his family? His friends? Alone? With pets? If he doesn’t do anything but sit in his bedroom playing Call of Duty, it might throw up some red flags, but at least the conversation is flowing!
7.   Tell me about your family.
People can usually go on forever about their family. Whether he has stories about growing up, about how he gets along with his siblings, what his parents are like, etc. How he talks about his family is important, because it gives you a better understanding of his life and whether he’s a family-oriented type of guy.
8.  What would be your dream job?
This could bring out some rational answers like being a teacher, or it could be more far-fetched like being a professional beer taster. Whatever their answer is, it gives way to plenty more questions about their idea of a perfect job!
9.   What’s the most spontaneous thing you’ve ever done?
Spontaneity is not everyone’s forte, but most people will have a story about something surprising or impulsive they’ve done during their life. But remember: some people’s spontaneous is another person’s normal day-to-day activity, so don’t be too quick to judge!
10.   What are some of your weird quirks?
Usually you try to hide these quirks until a few dates down the line, but it can be fun to bring them out early on. Yeah, you might come off as a weirdo when you tell him about your obsession with wearing hats because they make you feel safe, but he also might find it endearing.

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