Afternoon to all of our great members! I’ve been thinking about first dates and all of the potential anxiety that goes along with them, I came up with some of the best conversation starters for a first date that I think will have both of you learning a lot about each other without it seeming like an awkward interview. Let’s face it: Sometimes even the best date will have a ‘Is this an interview?’ moment. These are also good tips for things to sprinkle in through your date if you ever run into a lull in the conversation and they are also not intended for you to ask right away and one after the other.

What are you reading?

One thing that I like to ask is ‘What are some good books that you’ve been reading lately?’ This is a good icebreaker that will tell you a lot about each other, even more than you might originally think you’re finding out. It tells you if your date is literate first off, what sort of books he is into and also if you guys have anything in common between them. There’s a reason why book clubs are good places to meet men. If a man is able to converse well about books he’s reading, then that will tell you a lot about his thought process and how analytical he is. These may not be important traits to you, but clues about them are ripe for the picking if you so desire.

What was the best day of your life?

I also think it’s interesting to ask him what his best day ever was. This will give you some insight into his past and also show you what he deems important in life. It might be a tricky question to come up with an answer to on the spot, so don’t be surprised if it takes him a few moments to come up with an answer!

Who would be your dream dinner guest?

Asking someone what his ideal guest to have at a dinner party is an interesting one, too. It’s a lot more exciting than ‘What type of food do you like best?’ or similar, though this might become part of his answer. It also tells you more about him. If he were to choose a philosopher as a guest, for example, or if he were to choose Snooki… There’s a big difference in those two answers.

What’s your favorite place in the world?

This is a pretty generic first date question but it does provide some interesting possibilities to learn more about your date without you having to pry. For example, if he hasn’t done much traveling in his life then he may have a long list of places he wants to go, which opens up a whole other conversation without you even intending to do so. It also provides a nice way to have some back-and-forth between you because it opens up the door for you to discuss your travel experiences. It will also tell you if you have anything in common with him in these areas. If he chooses somewhere in the world that is the last place you’d ever want to go to yourself then he might have a hard time convincing you why he likes it so much, which could lead to an interesting discussion. If he’s more sensitive his answer might not be a city or destination but more of a small spot somewhere in HIS world that means a lot to him. An answer in that realm will reveal a lot about him, which is pretty juicy to get on a first date.

What’s your dream job?

When it comes to what he does for a living, I think it’s a lot more interesting (and strangely polite!) to ask him what his dream job is, rather than what his current job is. In an economy that is still far from recovered, most people are working jobs that are far from what they would like to be doing and this shows that you aren’t concerned with what he does, lest he think you might be put off by him telling you he’s working as a waiter but is really an actor. Hey, times are tough out there. If your date happens to have his dream job, then all the better! It’s great to be with someone who feels fulfilled in his career but it shouldn’t be that important to you either. Phrasing the question this way lets him know that.

Where do you feel relaxed?

Another conversation starter that I keep in my pocket in case the conversation starts to lull is asking where he feels most relaxed. This might sound like a boring question but I bet the answers you’ll get will surprise you. They will give you an indicator of how relaxed he is in general or if he has a bunch of answers at the ready for ways to de-stress. Depending on your own stress levels, this answer could be practically a deal breaker. Some people thrive under stress and find the same with their relationships and others want to do anything they can to avoid getting near anyone who is stressed out. Which camp are you in?

What do you think of these questions? Would you feel comfortable asking them on a first date? If not, what are the questions you like to ask or be asked on a date? It’s important not to make it seem like you are prying or asking questions that might be better off on a third or fourth date. You can also gauge his comfort levels based on the sort of questions he is asking you and by his responses to the first couple that you ask him. Some people are just naturally more chatty and conversational than others, and that’s something you should consider. Also remember that a first date is rarely going to be the most comfortable thing for either of you so don’t stress too much if his answers don’t impress you right away. Write and let me know your thoughts and be sure to discuss them with other guys in the chat rooms of ManPlay. You never know where that conversation may lead. You might get a chance to ask him in the flesh before you know it. Good luck!

John xo

Categories: Gay Dating Terrence