19. What Is Your Favorite Food?

Asking about food choices has a dual purpose. First, food is always an easy subject to discuss. Second, this helps set up future dinner dates and outings. It’ll also help to find out about allergies as well. It might seem like a random question but asking about food is the way to a man’s heart. 

20. What Is Your Dream Vacation Spot?

Discussing dream vacation spots also serves two goals at one time. First, it’s a great conversation starter. Also, it’ll set up future vacation plans. He may want to travel through Europe, relax in Hawaii, or party in Las Vegas. Maybe even all three places. It’ll reveal a lot about his personality as well.

21. What Is Your Favorite Song?

Another perfect question to ask a guy is about music. Sometimes, asking a simple question is the easiest way to make someone feel more comfortable. However, the types of music a guy listens to show his deeper side. It’s also wise to make sure they have good taste in music. 

22. What Is Your Most Embarrassing Moment? 

Everyone has that embarrassing thing that they wish they could forget. However, it’s not the worst thing to ask. Indeed, they’ll feel more comfortable opening up, especially if there’s no judgment. It’ll probably be a funny story and help the relationship grow closer. 

23. What Is the Craziest Thing You Have Ever Done?

Finding out the craziest thing a guy ever did can be very eye-opening. Perhaps they did something adventurous, like skydiving, bungee jumping, or running with the bulls. Maybe they eloped in Vegas, started a riot, or committed a crime. Perhaps they never did anything crazy and are looking for someone to bring it out of them. 

24. What Is the Last Thing You Would Do If the World Were Ending in 24 Hours?

If the world was ending in 24 hours, what’s the last thing you do? It might seem like a silly or random question, but it’s much more than that. It’ll reveal a guy’s priorities. Perhaps, he wants to take in one last sunset with the love of his life. However, he might want to play Call of Duty with the boys one final time.