The first couple of dates with a new girl can be awkward, but they’re a lot less awkward when you know the right questions to ask to get the conversation going. It’s not just about asking the right questions either. It’s also about knowing what you want to get out of the date.
So what are you trying to accomplish with these questions?
- Comfort: You want her to feel comfortable around you. By comfortable, I mean making her feel relaxed and safe with being herself and sharing her stories with you.
- Rapport: Your best date questions are ones that allow the two of you to have a conversation, get to know each other, and establish rapport. This is why open-ended questions are better than closed questions.
- Banter: Making a girl laugh is one of the best ways to get her talking, but funny first date questions can be hard to figure out. However, not every question you ask needs to be funny. Just try to stick with the type of humor that fits your personality.
- Sexual Tension: When the date starts going really well, it’s good to move into questions of a sexual nature. Keep it tasteful so you don’t freak her out, but you should be making an effort to let her know that you’re interested in her in that way.
1. Travel: “Where have you traveled/Where would you like to travel?”
These questions will work whether the girl has traveled a lot or simply wants to travel a lot. Talking about where you’ve been and where you’d like to visit some day gives you both the chance to talk about valuable life experiences you’ve had.
2. Childhood: “What do you like about where you grew up?”
I think this is one of the best first date questions to ask because, rather than simply asking where she grew up, it’s open-ended and allows the girl to tell you something about her life that provides context on who she is today.
3. Personality-Specific: “What’s your ‘Shark Tank’ idea?”
An outside-the-box question like this will require her to give it a bit of thought before answering, which is a good thing. A similar question might be “If you could have any superpower, what would it be and why?”
4. Dating: “What are some of the worst pickup lines you’ve heard lately?”
With this question, not only does she have the opportunity to vent to you and you have the opportunity to listen and be understanding of her, but you’ll also get to have a good laugh with her about her answers.
5. Kissing: “What makes for a good kiss?”
One of my favorite flirty questions to ask a girl is this one because it takes the romance and chemistry to the next level. You’re letting her know you’re interested as well as getting some useful information.
6. Sex: “What’s your safe word?”
Yes, it’s OK to talk about sex on a date, sometimes. There are dirty questions to ask a girl that work, and then there are ones that don’t work. “What’s your safe word?” happens to be one that works really well. I tell guys to use this one all the time because it allows them to transition from funny to sexy. A lot of what makes this work is the delivery. If you ask in a half-joking-but-not-really sort of way, she’ll laugh and you’ll laugh and you can turn up the heat.
Again, the important thing isn’t necessarily specific questions to ask on a first date (or second or third). It’s what you want to accomplish with your questions. Don’t be afraid to have a few questions you ask all the time, but always follow the conversation where it goes and adapt as needed.