The Good, the Bad, and the Ugly When Asking Dating Questions - Page 2 of 5 - Cool Dating Advice

The Good, the Bad, and the Ugly When Asking Dating Questions

18. What would you do if you had a million dollars in your pocket right now?

Women with million dollars what would you do dating

Insert a little joke in here about how heavy a million dollars would be. Maybe say something like it would bog you down, and you couldn’t do anything.

It is interesting to know what someone would do with a large amount of money. Do they give it to charity? Maybe they buy their parents something that they’ve always wanted?

The worst answer they could give is that they would buy themselves a $100,000 car or something really shallow with it.

17. You’re taking a road trip from one part of the country to the other… What five CDs would you bring to listen to?

Do people still listen to CDs? You get the drift. Ask them what albums or mixed tapes that they would listen to while traveling from one part of the country to the other.


Knowing what type of music your date is into is important for those many years when you’re spending quality time together. Do you hate country music? If so, then you need to find out now if that’s what they spend most of their time listening to.

A person’s musical tastes say quite a bit about who they are, and this is one of those questions that provide some useful insight into their inner self.

16. What toppings do you like on your hot dog?

What does it say about a person if they like something strange on their hot dog? Maybe your date likes to slather mayo all over their hot dog.

Depending on where in the world you live, your date might like a heaping helping of saurkraut on top of their dog.

The plainer the topping selection is, the more likely they are to have a very drab personality or maybe they just have intestinal problems.

Someone who likes their hot dogs fiery hot with spicy peppers is a person who maybe lives their life in the fast lane.

15. What as the last book that you read?

Some of you might not read books, and there’s nothing wrong with that. We live in a busy world where people don’t have the time for luxuries.

If self-improvement is a big thing for you, then you definitely want to know what book they read last. Also, ask them who their favorite authors are. If the two of you enjoy some of the same writers, then a whole conversation will begin over your favorite books and the characters in them.

14. Where would you go on a dream vacation?

Knowing where someone would go on vacation is a fun question to ask. Also, ask them what they would do there.

If they say their dream vacation is in Switzerland, ask then what’s so fun about there? What would they do while in Switzerland? Who knows, maybe someday the two of you will find your way to the Swiss Alps while drinking a mug of hot chocolate.

Stranger things have happened in life, and it might happen quicker than you realize.

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