April 29, 2023
By: Jerry Miller

First Date Questions to Ask for a Fun and Memorable Evening

First dates can be so exciting…but also terrifying and confusing. On the one hand you are looking forward to a fun night out but also wondering how to figure out if a second date is warranted without a full-on interrogation. Being too forward or asking some serious questions too soon can make your date feel as though you are rushing things. BUT. As an adult, you probably already know what you are looking for. You know what you need from a partner and where you want to be in five years. Dating gets tricky as we age because most of us just don’t want to waste our time, so there’s kind of a need for police investigation-level questioning. 

Don’t worry, doll. I’m here to help.  

Here’s a few first-date questions (and an idea of how to work them into a conversation) that won’t feel like a Maglite-in-the-face to your date. 

Would you rather spend a night in or go out on the town?

You can work this into the conversation while talking about wherever you are at the moment. Like “This restaurant is nice! Do you prefer going out or staying at home?” If a woman tells you that she’d rather have a quiet evening at home, she’s likely looking for a serious relationship so you will need to make sure the two of you are on the same page. This is probably mostly true for men as well. In my experience, men tend to go out more to escape boredom and loneliness than women do.  

What’s the best meal you have ever eaten? 

This one is easy to bring up, especially if you are in the process of eating. Listen, girls, let me tell you something. If you are vibing with a man and he answers that question with “my Mom’s (insert food here).” You better learn to cook, real good, real fast. You got some big shoes to fill.

What’s the best part about your job?

You can ask them this any time they bring up work, which you know will happen eventually. Most people sneak in little hints at their priorities when answering this question. If the reply is something like “the best part of my job is quitting time,” then they likely work to live, not live to work. “I just like being outside and not trapped behind a desk” means that if you continue dating, you’ll probably need a pair of shoes that you don’t mind getting dirty. 

Who is your most important person?

Lead into this question after sharing your answer. Tell a story about your person and then ask them about theirs. Besides learning who their most important person is, which gives you some hints into what/who they value most. If the relationship continues, you’ll know you’re headed toward a serious relationship when you get introduced to that important person. It’s good information to have in your back pocket for future reference. 

 Are you religious?

Since this is a dealbreaker for some, getting this question out of the way early is good. If it’s important to you, share your basic beliefs first and then inquire about theirs. 

Do you want children someday?

Ah. The ultimate deal breaker that's also hard to just work into light conversation. Ease into this one by sharing a story about a child in your life or making a comment about a child near you at the moment like “that little girl over there is adorable. Having kids looks like it's a lot of fun, doesn’t it?” and if your date has strong feelings one way or another, their answer will be telling. HOWEVER, there’s one caveat here. If your date already has children and you have your heart set on having one of your own someday, I think it’s very smart and perfectly acceptable to ask outright how they feel about having additional children someday. 

Where is your favorite place in the whole wide world?

This is another question that will give you hints about their priorities without being too invasive too soon. If their response sounds like it’s straight out of a country song like, “from my front porch looking in,” it’s likely that they are comfortable with their life and appreciate the simple “little things” about every day. (Or they could just be an introvert or possibly an anti-social hermit. Just go with your gut instinct on this one.) On the flip side, if their answer is something extraordinary or unusual, it’s highly possible that your date is the type to get bored with the mundane fairly easily. Either way, their answer will give you an idea of whether your sense of adventure lines up with theirs. Can Mr. Couch Potato and Miss Packed and Ready to Go be a match made in heaven? It’s definitely possible with the right amount of compromise!

 At the end of the day, first dates can feel more like a job interview than a fun night out, ESPECIALLY, when it’s two mature adults who are looking for a serious relationship. It can be a little tricky trying to work-in important questions while maintaining a natural conversation flow. Hopefully these tips will help! Don’t forget though, if your date is interested in a serious relationship as well, they’ll have their own deal maker AND breaker questions to ask, so just relax.  Y’all just go with the flow and get to know each other in a way that is comfortable and fun. 

 It will all work out exactly how it’s supposed to!


Until next time…

Love y’all and good luck,

Kelly Ann