9 Good Questions to Ask a Girl on a Date

We all know the feeling: you’ve got a date tonight; your stomach feels like it’s full of bees; your nerves are jangling so much your hands are effectively unusable. You put on your most flattering shirt, and then you head off to the restaurant to see the girl with whom you may, if all goes well, end up spending the remainder of your days. ‘No pressure,’ you say to yourself when you enter the restaurant and find your date sitting at the table; and sit down, face-to-face with latent failure. A date conversation is like a minefield.

Here, follow these nine good questions to ask a girl on a date, which should bring the conversation, through its network of bombs, all the way home:

1. Were You Born With It, or Did You Use Maybelline to Get Your Face to Look So Gorgeous?

You should break the ice with such a pleasantry as this. Make a bad joke, but make sure you tell it with a wry smile on your face, which lets her know that you know that it is bad. Lead off with polite jocosity.

2. So Where are You from?

It’s good to takes things slow, to begin with. You might ask where she is from, if this is not already known to you; and, if you know the area, or have a couple of friends from there, you might then inquire into the school she went to, and try and establish a commonality by seeing if you share any acquaintances.

3. If Heaven were Just One Moment from Your Life on Repeat, Which would You Choose?

This question should evoke pleasant memories and diffuse positive energy. It might also prompt the disclosure of a private moment, and thus create a sense of intimacy between you.

4. Have you Seen Any Good films recently?

If you come upon a silence, pursue a safe line of inquiry such as this that should obviate the recurrence of silence. Try and find some common ground. Chances are she’s seen movies, and that you’ve seen a movie she has. This might lead to “What are your five favourite movies?” Such questions might be considered useful ‘backups’.

5. So are You, Like the Love Child of John Travolta and Shania Twain?

Such a question, phrased in such complimentary terms, will both flatter and open up a whole new area of interest – family. If you are a guy concerned with appearance, then you might try and steer the conversation towards the appearance of her mother – to gain assurance before you purchase the product, so to speak, of its durability.

I would hope that you are concerned with more important things than appearance, and are more interested in such a topic as madness in the family. Try and steer the conversation towards the periphery of the family, the aunts and uncles whose madness might one day, find perpetuation in a child.

6. What’s it Like Being the Sister of Such a Successful Bombshell as Katie Melua?

I imagine this question would provoke the following answer: ‘Oh stop it,’ accompanied with a flap of the hand.

7. If You had a License to Sleep with Anybody in the World …?

This question – its answer, that is – might give you the opportunity to say something self-deprecating; thus endear yourself to her. She might say John Travolta, for example, and then you can say, ‘Well I’m not John Travolta, I’m afraid.’

8. If You Found One of Those Monkey Paws, What would You Wish for?

This is another one of those platitudinous questions that might come under the heading ‘backups’. Your date has likely been asked this before and may have an answer pre-prepared. It is not likely to conduce to intimacy, but it will at least steer you away from the awkward.

9. Your Place or Mine?

You should only ever say this with a twinkle in your eye; unless, that is, you feel that you have really knocked it out the park.

In short, a conversation is a kind of art-form; and, like any piece of art, it should consist of the sweet and the sour: just as a song should have sourness succeeded by a sweet chorus, the conversation should consist both of agreement and disagreement. Do not be afraid to take exception: in fact, the conversation requires such friction, or else it will simply peter out. Just be honest and authentic. Good luck.

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