Most people say that the first date is usually the “make or break” of whether you’d like to see the person again. Either continue what started as something fun and harmless, or end the day with a handshake or a text that says “Thanks”, never having to see them again. If you’re leaning towards the side of wanting to see the person again, creating a light and interesting conversation with questions thrown left and right would most likely give you the feel for whether you both are compatible.
Here are some questions to ask on the first date:
“What do you do—besides your regular job?”
The person’s finally out of their office and a lot of people don't enjoy talking about their job. Let them talk about something they’re passionate about, and it usually shows another side of them. Their hobbies might even surprise you as being one factor of compatibility.
“Any plans for travelling? What’s the most interesting country you’ve been to?”
Considering whether or not the person you’re on a date with is a travel junkie, a country’s culture is definitely interesting conversation starter. If they haven’t been travelling, asking them what countries they’d like to visit and why they chose that country. This gives them the impression that you're adventurous and culturally aware of different countries whether you’ve been there or not.
“Are you a coffee person or an end-the-day-with-an-ice-cold-beer type?”
Let’s just say that this gives you a heads up about where you’ll be heading after dinner, in case your date decided to meet up with you for dinner first. Its not much of a conversation starter, but it does give you enough time to think of places to go after dinner to continue the date.
“Have you tried any good restaurants? What do you recommend?”
The best way to a person’s heart is through their tummy, so if you aren’t one to cook, this is a good way to find out your date’s favorite dishes and cuisines. This might even land you a second date at the recommended restaurant.
“Wanna split the cheque? Okay, can I at least be the one to tip?”
This is pretty much etiquette, considering this is the first date. It's always better to offer than assume that your date is paying for both of you. If they prefer paying for dinner, offer to pay for coffee or drinks.
These questions are intended to eliminate those unwanted dead-air and dead-end questions during the date, but these five light and conversational questions do give you enough information to know whether the compatibility is there. If the wavelength is interestingly mutual, the second date will come off easier for both of you, especially since you’ve had your exchanges of interests and hobbies. Your date may even have picked up a few ideas of where to take you next when you decide to see each other again.