First dates can be nerve-wracking. What to wear? What will he be like? What in the world will we talk about? Keeping in mind some of these questions to ask on a first date will help you comfortably ease into a conversation. And these conversations will determine if you connect enough for a second date… which will hopefully lead to the third date, and so on. There’s nothing worse than those long, awkward silences that can happen when two strangers struggle for conversation. This is where asking the right questions can make all the difference and why it’s good to have a few up your sleeve and ready to go.
There are some basic “no-nos” when meeting a man for the first time. You know, those questions your mother told you never to ask because it’s bad manners – religion, politics, weight, his job, and money. But, while tempting, you should also avoid asking him why he broke up with his ex. This will inevitably lead to an hour-long rant on his part, boring you to tears and buzz-killing the entire date. And there goes the second date.
Chances are, you will first meet your mystery man over the phone to iron out the details of your date. If you’re tempted to text this exchange, don’t. Hearing his voice will help you get a sense of him before you commit to an in-person rendezvous. If his Scottish accent sounds like Greek, or if he uses language you find offensive; hell, if you use language he finds offensive, etc., bow out now and save your precious time for Netflix.
When you do speak, tossing in some benign questions about his daily routine can reveal a lot about his personality, values, and humor, so you can decide if you want that first date in the first place. “Do you have kids?” “How old?” “Do you have pets?” “Do you play any sports?” Etc. This can also prepare you with more insightful questions to ask on a first date when the time comes.
First dates can be absolutely dreamy if there’s non-stop talking and lots of laughing. Now that you’ve sussed out his sense of humor and smarts on your phone call, you have a bit of a foundation to build an in-person conversation. You’ll forge a more meaningful connection if you ask questions that are meaningful to you. Ask lots of them! There’s nothing a man loves more than talking about himself. If he’s fun, funny, and interesting, there’s nothing we like more than listening to him.
Don’t bring up controversial issues. Common knowledge questions are nice to have in your back
pocket. “What is Wordle, and why is it so popular?” Remember, when the going gets tough, the tough bring up Space Stations, baby pandas, or Bennifer.
Asking him what he’s watching on TV can not only spark conversation but also give insight into your
compatibility. If he only watches sports and you love turn-of-the-century British drama, there’s not a lot of common ground. Especially if he’s eye-balling the Dodger game being broadcast in the bar behind you. However, if you both are addicted to Game of Thrones, you’ve got enough material for five dates.
If he’s into distance cycling and is training for Iron Man, chances are he’s not going to have a lot of
free time for you. But if you’re training as well, then that could mean more ways to connect. Or maybe he’s into something new and different that interests you. “Tell me about it.” If you’ve always wanted to learn to rock climb, and he’s super interested in bread-baking, BAM, there’s date idea number two all lined up.
(Or, “What’s your favorite place on earth?” Or, “What’s the best vacation you’ve ever taken?”) What I’m looking for is how he feels about travel. If he’s happy with a local camping trip every other August, some gals may not see their travel dreams coming true. Or if you like to stay close to home, and he wants to hang-glide off Mt. Kilimanjaro, then both of you are traveling solo.
Or maybe, “I like to go to bed with a clean kitchen; what about you?” Simply stated, is he a slob, or is he a neatnik? Either one may jive with who you are, but if it doesn’t, take your feelings on the
subject and multiply them by 100. Because that’s how it’s going to feel once you’ve been dating this guy for a year.
Or, “Who was the first person you kissed?” This one gets a smile every time – generally followed by an entertaining story. More importantly, this question is guaranteed to fill a flustered gap in the conversation.
Let’s think positively and assume that you do, in fact, like this man. Once you’ve loosened up and decided you’re all in for a second date, feel free to slip in some more heartfelt, personal questions.
These details can give insight into who he is now. Get him talking about his parents. I’ve found you can gauge a man by how he speaks about his mother. I once dated a guy who absolutely hated his
mother (Yikes!). Lo and behold, three months later, I was on the receiving end of some major anger (Swipe left!). Meanwhile, someone who was raised by decent people in a happy household will most likely treat you with kindness and respect (I know, there are always exceptions).
I love this question. It’s playful yet informative… You will not believe the responses you’ll get! I’ve gotten everything from “I’m an Eagle Scout” to “I’m still married” (Yep, I’ve gotten that one more than once). This question can be an awesome conversation starter, or finisher, depending on the answer he gives you.
So, the evening is winding down, you’ve finished that bottle of merlot, and the two of you are feeling pretty good. This is when you can get right to the point. “What are you looking for in a relationship?” You may as well dive in on the first date since you want to know if the two of you are on the same page on this all-important issue. If he has no interest in having a relationship, and you are done with the dating thing and ready to settle down (or vice versa), grab that last swig of merlot and get the check. Netflix awaits.
I know you’re a bundle of nerves, and your mind is all over the place, but make sure to listen to what your date is saying when he answers your questions. Not only is listening good manners, but it makes your date feel good about himself. This makes him want to see you again – if you so choose. If you listen carefully, chances are, you’ll have follow-up questions to ask on a first date.
But let’s be honest, when you’re on a first date, the one thing that’s better than a good question (aside from a good kiss) is a good laugh. If he’s trying to be funny, and he is funny, then give him what he longs for – your delightful giggle and that beautiful smile. He’ll relax, gain confidence, and laugh along with you. Then there you’ll be, the two of you, on your first date – conversing, connecting, and laughing together – all the while knowing you’d like to see each other again.
And is there anything better than that? That’s my question for you.