The first date. It’s a thick hunk of excitement, slathered in promise, sandwiched between two slices of stress. You have to look good . . . but not too good, so he doesn’t think you’re trying too hard. You have to flirt just enough to keep him tantalised, but not so much that he wonders if you’re the kind of girl who’d throw herself at a Good Friday Bobolee if it was wearing cologne and a nice suit.
Plus you have to find out as much as you can about him. Presumably, if you’re actually out with the man, you’ve already ruled out the possibility that he’s an axe murderer or an escapee from an asylum. But there’s a whole lot of stuff you should find out about him before you proceed to date two. And the only way to get information is to come right out and ask.
Here are a few questions that could give you X-ray vision into his mind.
What’s the scariest/grossest/most fun thing you have ever done?
This one will take him off guard. He was probably expecting you to ask about his job, his family, his marital status . . . but this? His answer will give you some insight into what excites him, interests, him, turns him off or on.
Good follow-ups are: And how did you deal with it? What did you learn? Would you do it again?
If you could go anywhere in the world, where would you go and why?
His answer can tell you how he feels about his heritage (does he want to visit the land of his ancestors?); his boyish fantasies (white-water rafting in Canada, photo safaris in Kenya); or his secret sexual desires (Bangkok, anyone?)
Another similar question: You have $1 million and one week to spend it. Go.
If you could do any job other than the one you’re doing now, what would it be?
This is a twist on the old “what do you do for a living” question, and one that won’t make him feel you’re busy calculating his net worth at the back of your head. His dream career will tell you where his ambitions and skills lie, and how creative he can be when it comes to dreaming big.
Other than your immediate family, what one person has had the most impact on you?
This is a good one because it will tell you what’s important to him: information, guidance, advice, encouragement, etc. It will also show whether he’s grateful for the helping hands he’s received in his life. There’s no such thing as a self-made man. If he shrugs it off and says, “Nobody. I got where I am all on my own,” he’s just fooling himself . . . but not you.
If you could have any superpower, what would it be and why?
Does he want to save the world, raise the dead, defeat bad guys? Cool. Does he want to crush his enemies with an indestructible fist, burn them to a crisp with his laser-beam eyes, and hear the wailing of their womenfolk? Run. Run fast.
Tell me about your longest-lasting friendship, and what keeps you two together?
His answer to this one will tell you what he values about his relationships, and whether he’s a good friend or not. (Remember, before he can become your lover, he’s got to become your friend.)
So there you go: a few questions to keep the conversational ball rolling without leaving him feeling blindsided. He’ll probably be grateful (and flattered) that you’re interested enough to ask. Don’t think about it as an interrogation, think of it as an interview . . . for the privileged position of Keeper of Your Heart.
Questions NEVER to ask on a first date:
- Do you want children?
- Do you think that girl over there is pretty? Prettier than me?
- Can I have a lick of your ice cream?
- This dress is ugly, isn’t it? I knew I shouldn’t have worn it. I shouldn’t have worn it, right? It’s okay, you can tell me.
- Is your brother single? I’m just asking because . . . well, I’m just asking. . . .
Comments? Any questions you’d like to add? What’s the worst question anyone ever asked you?
