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7 questions to ask on a first date and conversation starters for ANY PARTY


first date questions

I was reading the lasted edition of Cosmo (the hot pink with Nina Dobrev on the cover) and loved the article about ‘How to work the room AT ANY PARTY’. It’s on page 256. I especially loved the part on conversation starters by Rumi Neely, Fashion Toast blogger and Simon Doonan, creative ambassador at large at Barneys and author of fashion memoir The Asylum, out Sept 3.

Don’t be afraid to stand out. Doonan loves asking, “Have you ever been on a cruise and caught a horrible disease?” Neely picks up on things happening in the moment and makes a joke. “People feel more special, and it’s more fun.”

They list several questions like, “How many sweaters do you own? Tell me your most embarrassing nickname. What’s your favorite place to go on vacation? What’s the worst hair style you’ve ever had? Can you believe people wait in line for hours… for cronuts? What would you wait that long for?” All great conversation starters in my opinion. It’s incredible how much you can get to know someone and how much you bond just by asking different types of questions.


Forget just working a party… how can I use this for dating?

So I brought this up to my friend and we started giggling just thinking about it. We were laughing so hard about all of the craziest questions we had ever asked guys or been asked on dates. This spiked our interest so we went in search of more out of the box original questions besides “so what do you do for a living?” blah blah blah right? boring! and with a little direction from my friend I stumbled upon this little gem. A website called Sparks by April Beyer. She’s a great match maker and host of VH1’s Making Mr.Right.

And she wrote about 7 questions to ask on a first date with reasons behind why to ask them and what to take away. AMAZING. I was sold. So I decided to share her lovely advice with y’all!

The great thing is these questions are acceptable for a first date conversation (or any date really), and also have the added benefit of getting you vital information without making you feel like you’re conducting an interview. She put these questions in a month long 4 part series which I have so generously summarized and compiled for your reading pleasure below. Because April, that was way too many clicks for me. Love ya though.



You can check out April on her website Sparks! It’s packed full of amazing dating advice!

Want to know if this new man in your life has your sense of humor? Curious to know if he’s loyal, adventurous etc… To get the full scoop check out all this and more here!

Here’s an excerpt from her series!

Eight Questions to Ask on a First Date, Part 4

Let’s take a look at what can make or break a first date. I’ve listened to thousands of post-date stories from my clients, and most of the time people have the same two reactions to their experiences, depending on the outcome. If the date is successful, they are elated. If it all goes wrong? They are mystified.

So, what’s the difference? Believe it or not, the two reactions hold the key.

It all comes down to awareness. If you’re surprised by the outcome of a date, if you have no idea what your date thought of you or whether or not he liked you, then you weren’t really on that date. Well, you were there, just not in full. Perhaps you didn’t express or reveal certain things because you feared it was TMI territory, or you were worried about the image you were presenting. Maybe you wanted to ask an important question but thought it was too personal.

Whatever the details, the underlying reason dates fail is over-thinking and holding back. Just be you and be in the moment. Focus on getting to know the other person, who is sharing this moment with you.

And by all means, if you’re curious about something, go ahead and ask! Remember, it’s not what you ask, it’s how you ask. A question wrapped in warm fuzzy blanket of genuine interest will always go over well!

Last week I told you how to find out if a man is compatible with you and how to learn if he’s truly ready to be in a serious relationship. This week, I’m showing you how to discover if he shares your family values and if he’s completely over his ex. These are very touchy subjects but let’s face it. You want to know!

7. To Find Out If He’s Over His Ex

When did your last relationship end? Most people will tell you not to talk about past relationships on a date, but I say otherwise. As a Matchmaker I’ve met with thousands of men and I have to ask about their relationship history. I’ve yet to meet a man who didn’t open and up and give me the tell all.

Believe it or not, a date is not much different. I build trust with these men and so can you. You just don’t want to make the evening all about former relationships.To read the rest and get the full scoop, check out all this and more here!


So let me ask you. What are some outrageous, bold, break the rules type of questions you’ve asked on a date or to a stranger or at a party? Did it work? What was the outcome?