Updated: August 17, 2022
You’re on the right track thinking that these questions should be open-ended and not of the simple yes or no variety. But hey…what do cool people actually talk about? Here are six questions to ask that always seem to start a good conversation.
1. “Hey what’s with this on your profile?”
Choose one unusual thing about his profile and get more details on it. Choose the one thing that you like the most and use that as a springboard for a conversation. Maybe he said something unusual. So quote him and get him to explain himself. This usually works because guys take time creating their wordy profiles and are glad to steer the conversation towards their awesome life and perspective.
2. “Hey, that’s a cool shirt! What’s the story behind it?”
Compliment him with something original. People spend too much time talking about the most peripheral of all things. Good looks, big muscles, money and career, and so on. For a change, why not compliment him on something out of the ordinary? He may actually build on that conversation, if you choose the right compliment.
3. “That’s a kickass car. A Classic! Did I read that you built that?”
Ask about their hobbies! While work might be a downer of a conversation, people usually take pride in their hobbies. Does your crush frequently post works of art, personal projects, restored items, music or even pictures of his pet? Ask him about that! Get him talking about something he LOVES, not tolerates.
4. “I was watching (recent movie)…it was pretty cool.
Asking about the latest movie, book or song is another safe topic that can lead to a good conversation. The reason why this is a good subject is because it’s not overly personal or invasive. Some women make the mistake of asking personal questions WITHOUT first really bonding with the guy. When these questions come out of nowhere or are wanting too much personal detail, the guy puts up a shield.
5. “What are you looking for in a relationship?”
This is a bit of a drastic conversation starter, because it may make or break the emotional connection you have. It’s a very honest thing to say and honesty seems to provoke more honesty. Your partner may say, “Nothing serious” or may say “A long-term relationship.” Or maybe he’ll be confused and reply that he’s not sure what he wants.
6. So what does an ideal Saturday look like for a guy like you?
This is a seemingly innocent question that accomplishes two tasks. It gets him to describe his daily life and the things he does on his day off. It also opens up the opportunity for him to ask you out or at least attend an event together.
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