5 First Date Questions That Score BIG Everytime

First date questions don't have to be boring!

So you're nervously preparing for an evening out with a new someone.  And (of course) to brush up on your game (and prevent those sweaty palm awkward moments) you now find yourself searching madly for questions to ask on a date.  I've been there. (Hence the list of the following 5 first date questions)

First dates are well ... kinda hard.  If you're anything like I was, the day of,  you're mix of "nervous wreck" and "excited nausea".  You want things to go well but you're not exactly sure how this first date conversation is going to flow.

And lord knows you don't want to embarrass yourself.

In true Total Love Makeover fashion here are 5 first date questions that you'll not only feel comfortable with but that offer a refreshingly surprising twist on the norm.


Typical First Date Question #1: What Do You Do?

We all know out of all the questions to ask on a date this one is sure to pop up.  The problem with this question is that it's boring and expected.  Sure, you want to know what he does but you certainly don't have to ask like that!

Instead of the ultra dry

"So, what do you do?"

Try this Total Love Makeover twist for question #1:

"I could ask what you do, but that's a little to boring for my taste. So instead I'll ask what would you be so thrilled and amazed you're getting paid to do?"

If you find yourself thinking, this is a great first date question as far as questions to ask on a date go, but I really do want to know what he does.  Simple.  After he answers give this response a try.

"So how does that compare with what you do now?"

It's a natural fit for him to explain his current job and how it ties or doesn't tie to what he dreams of doing.

Why I love first date question twist #1:

In just one question you've allowed him to talk about something he's passionate about giving you a pretty good glimpse into what excites and drives him.  

This is also information that you can keep in your back pocket should you two decide to keep seeing one another.  If he dreams of being a sports announcer, maybe one day you send him a text with a microphone emoji.

"Browsed past sports radio on my way home today but it wasn't your voice so I kept browsing."


Typical First Date Question #2: Where Are You From?

And again as questions to ask on a date go, this first date question is bound to come up.  Truthfully i'm not sure why.  Do we really want to know where he's from or is it just a naturally convenient question?

Either way, here's a great Total Love Makeover twist for question #2

"So tell me a random fact about your hometown that people don't usually or wouldn't care to know."

Why I love first date question twist #2:

Often this question gives you a glimpse into your date's humor (or lack thereof).  

I once had a guy tell me his hometown was known for it's foul aroma.  The conversation that followed was surprisingly hilarious.

Just as a word of wisdom .... if you're going to ask it, you should probably also have an answer.


Typical First Date Question #3: What Do You Do For Fun?

Out of all the questions to ask on a date this one is probably the most informative.  Your date's answer to this question is going to give you a good glimpse into whether there's compatibility (not just chemistry) between you two.

So why muck it up with the bland and the boring?

Here's a great Total Love Makeover twist for first date question#3

"When your roll dog, best male friend comes in town what do you guys do to live it up?"

Of all the first date questions this one is my favorite!

Why I love first date question twist #3:

You can tell a lot about a man by what he spends his time and money on and HIS choice of FRIENDS.  

This is a whopper of a twist on an obvious question!  You're again giving your date a chance to talk about something he's excited about (which is always a plus), and he's peeling the veil a bit to tell you about his strongest friendships.

If he happens to tell you he doesn't have any good friends you can simply modify the question life so:

"No best buds in the man cave huh? Well what do you do to live it up?"

[As a caveat, someone who has good friendships is often more likely to have a healthy relationship. A man or woman who does not have many or any friends is more inclined to make a significant other their unhealthy "everything".  Here's a nice post on the importance of having good friends.]


Typical First Date Question #4: So Tell Me About Yourself

Ok, so while this isn't exactly a question it's certainly a comment that's overplayed and underwhelming.  The problem with "Tell me about yourself" is it offers absolutely no direction.

And while the asker is probably just trying to keep an already awkward first date conversation alive -  a statement like this is so broad it can be overwhelming to answer.

So tell me about yourself ...

(sweat bead) What do I say?  Is now an appropriate time to say I collect antique clowns? 

Give your date a fun focal point with this Total Love Makeover question #4 twist.

"Would you consider yourself a book, tv, or movie guy?"

Based on his answer, keep the conversation fresh and alive with this follow up:

"So what are your, do not disturb, must see live, shows this season?"
"What movie trailer have you been secretly watching on repeat, excitedly waiting for the release"

Why I love first date question twist #4:

This twist provides something fun and easy to talk about!  And a conversation starter like this is very unlikely to fizzle out quickly.  

If you've never heard of the suggested books, shows, or movies, a simple "I've not heard of that, what's it about?" will give you a solid continuation of good conversation.  

Plus you'll get to sample his taste in entertainment giving you an additional peak into who this mystery man is.  You may even be able to pick up some great suggestions.


Typical First Date Question #5: When can I see you again?

It's the end of the evening, you've had a great time and you think he's enjoyed himself as well so it's only natural to throw this question out, right?  

Well, as questions to ask on a date go this one can be the most awkward.

First date questions should be tailored as to not put pressure on the person answering them.  Ensuring a comfortable first date setting (on your part) gives you more chance of him wanting to see you again.

In addition to the question being pressuring, it's also pretentious.

He may not want to see you again.  In which case you've just put him on the spot to give an impromptu uncomfortable rejection, or come up with a little white lie.

Either option is no good.

Here's a great Total Love Makeover twist for first date question #5

"How's work for you looking this week? Do you have a busy schedule coming up?"

If you listen carefully his answer may reveal his interest in seeing you again. Emphasis on him being "really busy" and/or his inability to "have time for anything else" may be an indication he's trying to signal his disinterest.

However you can't know for sure without putting it out there.  Here's a follow up to the twist.

"I had a really good time tonight, if you're interested in doing this again sometime in the near future just let me know. I'd enjoy it."

Why I love first date question twist #5:

As far as questions to ask on a date go this one can be the most uncomfortable to ask and answer.  What I love about the twist is that it completely takes the pressure off.  

"Tell me about your upcoming week." is an easy question to answer and it also allows your date to throw hints of his interest in seeing you again.

The follow up is great because it takes the pressure off of him, allows you to express your interest, and gives him an unmistakable green light to ask you out again should he want to.  It's a win - win.


Remember first date questions don't have to be boring.  Keep the familiar, but add a little Total Love Makeover flair to the questions you ask on your date.

It's a refreshing spin on the norm ... and he'll never see it coming.


If you enjoyed this Love Lab post be sure to like and share.  And if you're ready to go a bit deeper in order to snag the love you've been waiting for be sure to join the Total Love Makeover Dressing Room.  


As always it's my pleasure to be helping you on your journey for love.

You can have the love you want.  Sometimes it takes doing something different to get something different.

Wishing you exciting, chemistry filled, first date conversations,