Flirty Questions

Whether you’re introducing yourself to someone or just trying to keep a flirtatious conversation going, it helps to ask questions.  If you’re looking for a reason to say hello, you should ask him a question about something relating to where to two of you are and what you’re doing.  Try to be funny if you can and keep it positive.  Don’t ask how his day was if you met at a funeral.  Don’t ask why he’s doing whatever he’s doing, as “why” questions can come across as combative and leave the person feeling like he has to defend himself.  Try to stick to questions that require more than a “yes” or “no”, because if you don’t, it’s likely that’s all you’ll get.  If he needs to give a more thought-out response, things are more likely to segue into a conversation. “How long have you been waiting for the bus?”, “Do you have the time?”, and “Do you know the way to [store name]?” can all work. You don’t need any fancy lines.  If, despite your best efforts, he only grunts you an answer then turns on his mp3 player, then you had better find someone else to talk to. 

If your first question spawns a conversation, there are others you can ask to further it.  Try asking her where she’s from, where she went to school, what her hobbies are, or where she’s travelled.  These sorts of questions are particularly valuable because they serve several purposes.  They give you a break in the conversation to be a good listener and absorb what’s being said.  You can learn more about the person and form a better idea as to whether or not she is someone you’re really interested in.  Most people enjoy talking about themselves, so he may appreciate the opportunity to discuss the topic on which he’s the most knowledgeable.  Finally, you’ll distinguish yourself as someone who is interested in getting to know him as a person.  All of these factors are likely to make a conversation run more smoothly. 

Part of flirting is showing the other person that you appreciate her, physically or otherwise.  This can be done by paying a sincere compliment.  These can take the form of a question, too.  “I love your jacket, where did you get it?”  “Where do you get your hair done?”  “That’s a great essay topic.  What gave you that idea?”  Not only will she likely be flattered that you’re impressed with her appearance and accomplishments, but it will give her another excuse to talk about herself.  Don’t overdo the compliments, though.  Shyer people can find them embarrassing and giving too many can give the impression that you’re too involved (and make people feel uncomfortable). 

Even more important than complimenting is teasing.   Friends, family members, and lovers often show affection for one another by teasing.  You can try to simulate these feelings of closeness in someone you might not know all that well by teasing him. Ask questions about what his favourite sports/teams are, what he studied, his hobbies (if you haven’t already), or his favourite musical genre.  With the answers to these questions, you’ll be able to tease him for liking “silly” sport and rival team, his “dorky” interests, and “terrible” taste in music.  Smile and make sure it’s clear that your mockery in tongue in cheek.  If people are often unable to tell when you’re being sarcastic, you may want to skip this step as you don’t want to come across as mean or insensitive.  Don’t ask or tease about subjects you think might offend him.

Despite this advice, it’s important to remember not to ask too many questions.  If you do, you may come across as either trying to dominate the conversation or as trying to hide the fact that you don’t have much to contribute to it.  If you avoid that pitfall, however, and he responds positively to your questions, it’s time to ask the most difficult question so far: “Can I get your number?”