“What’s your favorite sport? Do you follow any teams?”
Guys love to talk about sports, and they’ll be more than willing to share the details on their favorite team. Asking this kind of question tells a guy that you’re willing to go halfway and that you’re not going to find his statistics-spouting boring as dirt. It will relax him immediately … and, if you like sports, too, it will be a match made in heaven.
“That’s a cool watch/shirt/pair of shoes. Where did you get it?”
The fact that you’ve noticed some aspect of his appearance will mean a lot to him. He’ll feel flattered that you’ve been checking him out, and examining it more closely will require that you lean close and do some light stroking for a closer look. This is a great opportunity to show how fantastic you think he looks … and guys don’t get compliments like that often.
“Have you ever done X?”
Your first date is when you start to find common ground, and comparing hobbies and experiences is the first place to start. Asking your date about his experiences can allow him to brag a little or give you the opportunity to bring up cool things that you have done.
“Have you ever been to Y?”
Everyone likes talking about places they’ve been. Ask him if he has ever been to a local hotspot that you enjoy. Maybe it's a club, a coffee shop, a museum, or even a park or hiking trail. If he hasn’t been there, and you are hitting it off by that point, he may very well see that as a suggestion to use when asking you for a second date!
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