I know I'm in the rare camp when it comes to this, but I love first dates. When I tell my girlfriends this, this always look at me in disbelief.

"I hate first dates," they'll tell me, "it's the worst part of dating. You have to small talk for an hour with a stranger, and try to seem like the best possible version of yourself."

Parts of this are true, but I think first dates are fun and exciting and guess what, I'm going to make a convert out of you. I'm starting a blog series about First Dates: the best ways to begin them, outfits to wear, and the questions I ask to skip small talk and truly get to know someone.

We're going to start this series off with questions and conversation, the most important part of any first date.

I like to use first dates as a chance to figure out if this person and I can talk well together, by asking good quality questions and...let's be honest, judging them on how they respond.

Oddly enough, after literally all of my first dates, my date will text me with some form of "wow, we really talked about a lot of different topics" or "you ask really good questions!". I wish that this skillset was as lucrative as coding or being good with numbers but alas...my talent lies where it lies.

(Btw the fact that Jeffrey Epstein comes up so much is entirely my doing…just try and ignore that haha)

So without any further ado, here are some good questions to ask on a first date (or any date).

1. "If you could design your own bar, what would it be/look like?"

My preferred scenario for a first date is happy hour after work. It's a casual and low-stakes way to get a first impression of someone, and it's always interesting to see which bar they suggest.

At some point in the date, comment on the appearance of the bar, and I like to ask, "If you could build your own bar, what would you have it look like/what would the vibe of it be?"

It's a fun question, I like telling the person how I would have a swanky jazz-club bar, with live music, velvet seats and old-timey dressed up cocktail waiters delivering you drinks in fancy and over-the-top glasses. The signature drink would be gimlets and champagne, and they would serve appetizers and dessert only because, let's be honest, those are the best parts of any meal.

You get to find out with this question what aesthetic your date likes, what drinks they're into, and what music they listen to. Also, you get to find out if they're "game" for this type of conversation, which I think is super important.

Sometimes I ask a person this question and they'll be like, "uh, I don't know...a sports bar?" and I'll know we aren't a great match because I like to ask imaginative questions, and they're probably more of a realistic than I am. Totally fine - different strokes for different folks!

2. "If you could take home one item from this bar to your apartment, what would it be?"

This is pretty similar to the first question, but easy to work into the conversation if there's a random object in the bar, or a cool painting somewhere. Once you both start talking about it, ask your date, "okay, if you could take that home for free or instead pick anything else in this room to own, what would it be?"

It's always interesting to see a room through someone else's eyes, and a lot of the time they mention items in the restaurant that I didn't even notice before, which is cool.

Then I'll ask sometimes why they picked it, or where they would put it in their apartment, and it's a fun game to talk about how you would fit a huge restaurant couch in your New York studio, or remodel your kitchen to fit an entire bar in it, stuff like that.

And if someone answers with, "I guess I would take the cash register because it has all the money in it," it's an easy way to know that we probably aren't the best match haha.

3. "What character from (TV show you both like) is your favorite, and which one reminds you the most of yourself? Is it the same character, or different ones for that answer?"

During most first dates, you'll find yourself talking about TV shows you like. Instead of just saying "yeah, I love that show!" and moving onto the next topic, I like to ask them about characters.

For example, if my date and I are talking about Game of Thrones, I'll say, "Which Game of Thrones character is your favorite, and which character do you think you're the most like? But let me know if it's the same character."

I think it's a great question because it shows who we are, and who we want to be with that question - in a light-hearted way! I love Daenerys in Game of Thrones, but I see myself in Jaime Lannister. It's kind of true, I see myself as a flawed person (Jaime), but I want to be a dragon mother with perfect hair (Daenerys) because....well, who doesn't.

Then you can ask your date why they chose that answer, who they are the most not like in the show, stuff like that!

Warning: If your date says, "I think I'm the most like Dexter," you might want to excuse yourself to the bathroom and get outta there.

4. "If you could own 3 houses throughout the world, where would you want to have them?"

Honestly, maybe this is less of a "date questions" post and more of a "the random things I always like to ask people" one, but still...I'm keeping this one because I like it a lot.

I love this question because it gets to show the different sides of someone's personality! For example, I would answer that I would want a penthouse apartment in Manhattan (go big or go home when it comes to hypothetical questions, baby!), a villa on top of a winery in Italy, and a cottage in Ireland surrounded by lots of land with sheep and goats and horses.

Then I would explain how I love New York and being a part of the city, but I also one day in life want to relax at a slower pace. I could bring up how I used to live in Ireland and I love the country, things like that. You get to talk about traveling and reference the places you've been before, as well as the places you want to go with this question.

Some people have told me that they want houses by the ocean for surfing, or houses in the mountains for skiing, so you get to find out about their hobbies too in a way that's a lot more interesting and cliche than asking "soooo what are your hobbies?"

There you have it! Four great questions to ask on a date. Keep in mind, these are questions that I like because my joy in life is asking people off-the-wall questions that aren't grounded in reality. If you're looking for someone a bit more serious, then I suggest asking something different haha!

Try some of these out and let me know how you like them!

Best,
S

Four unique questions to ask on a first date

1. "If you could design your own bar, what would it be/look like?"

2. "If you could take home one item from this bar to your apartment, what would it be?"

3. "What character from (TV show you both like) is your favorite, and which one reminds you the most of yourself? Is it the same character, or different ones for that answer?"

4. "If you could own 3 houses throughout the world, where would you want to have them?"