good questions to ask your date
1. “Hey, have you seen that new show that came out about such and such?”

It doesn’t matter if you have any interest in the latest show you saw advertised. The question is just a natural-sounding opening to a discussion of the TV shows he does currently watch and enjoy.

When he says he didn’t see the new show, you follow up with, “I might check it out. I’m looking for recommendations on a good show to add to the list I record.”

Naturally, that statement pulls for a recommendation from him. And that will be valuable information.

Because you may discover a point of common interest, which makes it easy to start conversations in the future. Or, if you’ve never seen the show he recommends, you can start watching the show he enjoys. “Hey, you got me hooked on that show. Did you catch that last episode?”

There’s a formula at work here. You can use it for lots of different things.

Basically, the formula is this: Ask about something very specific. Then use the ensuing conversation as a segue to learn something about his life. You get inside information about what he likes without seeming like a creepy stalker.

An alternative example would be, “Hey, have you ever read (fill in the blank)?” Followed by, “No, I haven’t either; I was just wondering if it was any good. Have you been reading any good books lately that you would recommend?”

There’s nothing quite like having something in common to spark easy conversations that are genuinely interesting to both parties. That feeling of having something in common naturally leads to further development of a relationship.

2. “What brings back a positive feeling of nostalgia for you?

This question not only sparks an interesting conversation, but often leads to information about his personal history. The question might also lead to a great idea for an inexpensive and meaningful gift when his birthday rolls around.

3. “What’s your problem?”

It sounds like a joke, but I’m not kidding. While you wouldn’t phrase it this way, the gist of the question is focused on getting him to open up about the top thing that has been bugging him recently.

As soon as a man starts to lean on you for emotional support, you become more significant in his emotional world. That can open doors to greater intimacy.

How to seamlessly integrate this question into everyday conversation is a topic for another day. For now, just use your ingenuity and watch for an opening.

4. “I bet there’s another side to your personality that a lot of people miss, isn’t there?”

There are two ways he can answer this question. Before I get to those, let me preface my explanation by saying that the vast majority of people actually do feel they have qualities (or less dominant personality traits) that most other people fail to see.

The first way he can answer this question is something like, “Why, yes…actually there is. Everyone thinks I’m quiet, but if they would ask me a question, they would discover I have a constant flow of ideas in my mind…sometimes so many ideas I don’t have time to verbalize them. So they assume I’m quiet, and it drives me nuts when people misperceive me that way.”

If he reveals something like this, you have just discovered a way to connect with him that most other people cannot compete with. You have inside information about how he perceives himself (realistic or not).

good questions to ask your dateWhen you’re the only person in the room that really understands something about his internal world, you seem more significant to him. He will feel less alone in your presence because you’re one of the few people who understands his true nature. Little does he know; you didn’t understand his true nature until he told you about it.

The other way he can answer this question is, “No, not really. Why do you ask?”

To which you would respond, “I’m not sure. If I could tell you what it was, I wouldn’t have to ask. I just get the sense that there’s another side to your personality beyond what most people perceive.”

This response will get his mind spinning on these questions. He’ll ponder this question because it’s an open loop. The mind likes to close open loops by resolving unanswered questions.

Unanswered questions pop into the mind automatically and without bidding far more than problems that have been solved. As a result, the question will enter his mind frequently (along with you) which will cause you to become a “somebody” rather than a “nobody” in his mind.

5. “Hey Tom, got any fun plans for the weekend?”

This is a question that becomes more useful the more often you ask it. For someone you don’t know well, you will likely get a vague response the first time you ask this question. But soon he will relax, as he realizes you’re not trying to intrude on his weekend plans by inviting yourself to join him.

He will begin to see it as your playful way of making small talk with a cheerful topic. It won’t be long before he starts giving you specific details about fun things he is planning for the weekend, like a plan for some Whitewater kayaking with two of his buddies on Saturday.

Once he’s comfortable talking with you about his weekend plans, it’s only a matter of time until he realizes one of his plans could easily include you. He just might invite you to come along since the plans are already a topic of conversation. The barrier to asking you out has been eliminated.

Naturally, you will need to tailor these ideas to the particular person and circumstances in your life. But I hope a few of these questions will spark some creative ideas for deeper connection.

Always on your side,


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