Introduction

Hi, friend! We’re glad you’re thinking about coming to one of our events. It can be tough finding people to date, especially when you’re out of pratice when it comes to meeing people face to face. But don’t worry! We’ve got plenty of non-akward conversation starters to use at a dating keep things interesting. Feel free to call some of these ideas your own or rework them into your own style and personality.

1. I think this might be the most awkward dating event I’ve ever been to.

You’re not alone in thinking this is the most awkward dating event you’ve ever been to. You also might be wondering why you were so excited about it in the first place. First off, let me say that I know why you’re here: because someone told you that it would be fun and exciting and maybe even life changing. Second, don’t worry about making a fool of yourself by being overly enthusiastic—that’s what everyone else is doing!

But really, don’t worry about making a fool of yourself. If anything happens tonight (and we’re sure it will), just remember that this isn’t real life; this is an experiment with no stakes involved—just like any good game show would tell us. And if nothing happens at all? Well then at least we had one helluva good time playing along!

2. There’s this great restaurant a couple blocks from here. Have you checked it out yet?

There’s this great restaurant a couple blocks from here. Have you checked it out yet?

It’s called the “Jerk Off.” It’s a Jamaican restaurant, and they serve their jerk chicken with garlic rice, plantains and mango salsa on the side. It’s a very casual place — there are picnic tables outside where you can sit while enjoying the fresh air and cool breeze coming off of the water nearby. They also have an indoor dining area that has some exposed brick walls so that it feels cozy inside even when it gets hot outside. Plus, if you’re in the mood for something sweet after dinner there are always delicious desserts like rum cake or brownie sundaes made with vanilla ice cream and caramel sauce on top! I really enjoy going there because everything tastes great but also because I love how unique each dish is (like when I tried something new last time: fried plantains topped with cheese sauce). When we go together we usually order two entrees so we can share both—that way we get more variety!

3. So, tell me about your best friend…

So, tell me about your best friend…

This is a great way to get to know someone. It’s a question that shows you’re interested in getting to know them and not just what they do for work, but who they are as people. Asking about their best friend can help you understand the person more than a simple question like “What’s your favorite thing about working here?” would.

You might also want to ask about their relationship with their best friend: Do they have tons of mutual friends? Are they close friends from childhood or college? How long has it been since they’ve seen each other? What are some of the things that make them so close—and why do those things work so well for them?

Another good thing to ask is how personality-wise, their BFFs are different than themselves (and vice versa). For example: If both people tend towards introversion but one is super social while the other prefers alone time, it may be interesting for those two types of personalities to come together! Be sure not only discuss similarities between yourself and others but also talk about differences too!

4. What should we all be doing right now instead of being here?

This can be a great opportunity to talk about the things you love. You’ll want to get specific, so if you’re both into music, list some of your favorite artists and songs. If one of you is into hiking, mention what trails are near by. If one of you loves exploring new restaurants and bars in town, suggest checking out a new spot together sometime soon (it’s easy to find this info online).

If there’s anything that would make this event better for both of you—and if it’s not too late in the evening—why not do it right now? Go have dinner at that place with the best burgers; go see that band playing at a local bar tonight; grab tickets for opening night at your favorite theater company’s latest production; go grab ice cream cones with sprinkles on them from that shop down the street.

5. What kind of person are you hoping to meet right now?

Are you looking for a soulmate? Someone to share life with? Or are you just hoping to meet someone new, who might not be your future spouse (but could be—who knows!), but may nonetheless enrich your life and fill some of the gaps that currently exist in it?

It’s important in any conversation that begins with “What kind of person are you hoping to meet right now?” to stay open-minded and honest about what it is that you want at this point in your life. But don’t overdo it! If the event includes a very specific icebreaker or starter question like “What do people usually ask when they first meet each other?” then by all means feel free to riff on that if it feels natural. For example: “They usually ask me where I’m from.” “That’s funny because I’m actually from [someplace nearby].” Weaving in details about yourself helps paint an image for others so they know who they’re talking too (and also shows off their knowledge). And remember: small talk doesn’t have to be boring! It can actually be fun if both parties are willing…

6. How long have you lived in [the area]? Do you like it here?

“How long have you lived in [the area]? Do you like it here?”

This is a great conversation starter to get the ball rolling. It’s easy and straightforward, but can also lead to some deeper discussions about what each of you likes or dislikes about the place where you live. If someone has only been in town for a short while, they might be able to tell you some interesting stories about what’s changed since their arrival. They may also have inside knowledge of things that make one neighborhood better than others (like whether there are good restaurants nearby). If someone has been living there for a long time, they might be able to offer advice on how best to navigate city life—whether it’s important for newcomers to know how traffic patterns work or which neighborhoods are cool with kids riding their bikes through them at night.

7. What’s the last thing that made you laugh out loud?

The last thing that made you laugh out loud?

Whatever it is, chances are other people would like to hear about it. This is a great way to start a conversation with someone new and possibly build a rapport. The next time you go out for a date, try sharing something funny with your date.

8. So what three things would you bring with you if you were going to be stranded on an island with just a couple pieces of luggage and no other supplies? (But no, you can’t bring any other people!)

A conversation starter like this will get you talking about your interests. It also gives you a chance to tell a story and share something unique about yourself, which is crucial in creating a connection with someone. In addition, it’s an opportunity to find out that the person you’re talking to has similar passions as you—which means that if things go well, there are likely other activities or interests that could bring the two of you closer together.

This question provides insight into what type of person this person is without directly asking them questions like “what do you do for fun.” It also gives them an opportunity to show off their creativity and flex their storytelling muscles without feeling pressured into saying anything too personal or revealing (like how much money they make).

9. What was your favorite band/movie/tv show in high school?

• What was your favorite band/movie/TV show in school?
• What was your favorite activity in school?
• What was your favorite teacher in school?
• What was your favorite class in school?
• What was your favorite book in school?

10. If we were at a bar right now, what would you order for your first drink, second drink and third drink? And can I get those from this excellent bartender next to us?

The first drink should be something general like a beer or wine. The second drink can be more specific, such as a vodka tonic if you’re feeling fancy. The third drink should really show off who you are as a person, so maybe try an old fashioned if you have some time to get comfortable with your date and don’t want any more than that!

If this sounds like the perfect set-up for a good time, then I’d love for you to join me at my friend’s party!

Conclusion

Dating can be really awkward, but it doesn’t have to be! If you’re feeling nervous about meeting someone new in person for the first time, try these conversation starters. They’ll help you break the ice and get to know each other better without being so uncomfortable.