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Get to Know Your Date — Fast

The first few minutes of any date means getting past that awkward, shy stage. Unless, of course, you already know him and dating is merely an extension of your friendship. Most of us, though, barely know the guy we’re meeting for a first date. So, you need a dating strategy. A mental list of questions you can fall back on to kick-start the conversation should you find it flagging or reaching the awk stage. Plus, as long as you listen to his responses, they are a good way to help you get to know your date.

We’re not suggesting you interrogate him mercilessly, or put him on the spot. You don’t want to get into too much personal territory either. He’ll either share in a natural way, or he might avoid getting into all that on a first date. These are conversation starters, so should you both veer off into other territory, then that’s fine. Let the interaction flow.

And of course, we’re talking about guys because we are girls, but these questions work well for women too.

Get to Know Your Date — Fast

1. What would your ideal day look like?

Have your ideal day planned too, he’s bound to ask you the same question in return, so be imaginative. At the same time let it be realistic so he can jump in and say, “Hey, I’d like to go there too. Maybe we could do that together sometime?”

2. What is the most important thing in your life?

Be prepared to ask him some more questions especially if he talks about work, or his family, his friends, or his passionate weekend activity. And, of course, be ready to share the most important thing in your own life.

3. Who makes you laugh?

He may cite some well-known comedian, or he might tell you his best buddy, or even his little sister, is the one who makes him laugh the most. Ask if he can remember some of the funniest times. Share your stories too. Let the anecdotes flow.

4. Have you got a bucket list?

What does he want to achieve before he dies? Where would he like to visit? What would he like to try? Have your list ready too so you can compare notes. Bucket lists are fertile ground for keeping the conversation lively so you can get to know your date.

5. Who was your best teacher at school (or elsewhere) and why?

His answers to this can be revealing and can lead to all kinds of stories about his schooldays, or maybe college and/or university.

6. Are you a dog person or a cat person?

Always a good one to get them talking about their current or former pets. People can tell you so much about themselves when they are discussing their pets. You wouldn’t want to date someone who hates animals, would you? If they like dogs, ask them about their favorite dog breed. What dog would they own if they had the chance?

7. What is your proudest moment so far?

What did he do that made him burst with pride? What did he achieve that made his mother burst with pride? Maybe he saved someone’s life? Or regularly donates blood? Or volunteers for a good cause? Or maybe someone else did something amazing that made his proud to be associated with them? How about you? Have you got a proudest moment you can share with him?

8. What’s the worst trick someone ever played on you? Or you on someone else?

This is another great question to get those anecdotes flowing. See how animated he gets as he describes how he and his buddies treat each other. Or maybe the question will lead to Halloween, and what adventures he got up to as a kid.

9. What’s the weirdest dream you’ve ever had?

Everybody has got a weirdest dream. One that stays in the memory forever. Asking about dreams can open up even more avenues of conversations. Why does he think we dream? Does he believe in the afterlife? Has he ever received a message in a dream?

10. After you’ve taken care of your family, what would you do if you won the lottery?

This question can kick off a lot of fun chatting. See which one of you can come up with the craziest idea. Who would you help? How many houses would you buy? Which band would you hire to play a gig for only you and your friends? Where would you go for the best vacation? Who would you take with you?

11. Beach? Mountains? City? Where do you prefer to chill out?

You can add in: what’s the most exotic/unusual place you’ve ever been? What’s the most unusual place you’d like to visit? Have some interesting facts about Iceland to hand.

12. What’s your favorite food?

Dessert or main? Exotic or plain home cooking? Favorite food from childhood. Favorite type of restaurant. And, of course if you are both having a good time, this question will nicely lead to a second date. Never fails.

Five Dating Conversation Tips:

  1. Don’t turn it into an interrogation. Yes, you are asking questions, but let them flow and become part of the conversation. If you are not sure how to do this, just say, “I have a question for you…”

  2. When you’ve asked a question, give your date time to answer it. And listen.

  3. People love it when you are obviously interested in what they say, so unless this date is a total bore, give them the benefit of your attention. It’s the least you can do.

  4. Be ready to share your own stories, experiences, and anecdotes. But try not to talk over your date in your enthusiasm to share. Again, listen.

  5. On a first date, avoid talking about your exes and past relationships. There’s plenty of time for that later. For now, focus on getting to know the person in front of you.

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1 Comment

Shaun Barefoot
Nov 14, 2021

I remember these questions. Which person agreed to talk with me? I remember saying answers to majority of these questions. I'm not sure if she remembers asking me these questions but what was her name? The conversation was on August 18th, 2020

When there was a guy in my backyard while it rained for 4 hours. The probability of him coming into my house. Well, he didn't come in but he did get caught coming out of the red roof inn heading into South Carolina.

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