Questions To Ask On A First Date

Susan

March 28, 2025

Knowing the right questions to ask on a first date will always lead to a fun date and a 2^nd date. When it comes to first dates, as a matchmaker, I have heard about many first dates that go wrong. I have had many people come to me seeking our services because they can’t seem to get past the first or second date.

You need to know the questions to ask on a first date that keep it light and fun and create a connection and spark. Too often, singles interview their date like they are applying for a job. They might even feel they are applying to be your SO, but I can tell you there is a wrong way, and there is a right way to ask questions on a first date.

Online daters bring a lot of bad habits to a first date!

I have heard of singles bringing checklists to their date. The rise of online dating apps have led to a lot of bad dating habits. Singles feel they are trying to weed through many people, and get to know them quickly to assess if they are relationship material for them. They think this is the only way to know them by grilling their date.

Can you really get to know someone on a first date? This comes off as boring, and doesn’t usually result in a 2^nd date. You have to spend time with the person to have things develop naturally. Remember, you can’t pick a flower before it blooms.

Icebreaker Questions to Ask on a first date.

If money were no object, what would you do with your life? Thisreveals their values and tells a bit about the person.
Coffee or tea? Wine or beer? You might not even have to ask this question because when they order, you might already have the answer.
What’s the best vacation you ever had and where was it?
What’s your dream job?

Questions on a first date that are fun and light hearted:

Are you a morning or a night person? That’s always interesting.
If you had one superpower, what would it be? It’s just interesting to hear what your date says.
Are you more of a planner or are you more spontaneous. This one can be flirty, too, because you can ask them to do something spontaneous and you guys go for it whether it becomes going elsewhere or just something daring.
What emoji are you going to put beside my name in your phone? It’s a little flirty.
Are you more of a beach or mountain person? People love this question because it reveals more about the person.
What was your first job and what did you like about it?
If you could go out on a date with anyone, who would it be and where would you go?
Who’s your celeb crush?
Who was your first kiss?
What’s the most romantic kiss you ever had? I love this question because even though you are hoping to establish a romantic connection, it takes them back and puts them more in a nostalgic mood.
Tell me two truths and a lie. Sounds boring but it can be hilarious.

Relationship Questions that reveal love and values

Tell me about the one that got away? This involves an ex but It’s not usually the most recent ex.
What do you value most in your romantic relationships?
What’s the best advice your Mother or Father ever gave you?
Do you wish you had more siblings or less?

Biggest Dating Mistake To Avoid: Don’t talk about You Ex On Your First Date

Now that we gave you some fun questions, just remember to have fun on your date and be yourself. We aren’t trying to prevent you from being you.

Do remember to never have a conversation about exes. They don’t belong in your date conversation. Too many people do it, and it’s one of the biggest first date mistakes that you can make. Just say it’s a boring story for another time.

How Matchmaking Can Improve the quality of Your First Date

In matchmaking, we do help our clients and coach them along the way, and it definitely helps. I feel like the older someone gets, the worse a first date can be. Throw in a little ego and a longer life story that includes exes, and it can be the recipe for a bad first date.

First dates are for having fun, making a connection, and getting to a 2^nd date. If you need our help, just reach out to us and start having better dates now!