Five useful questions to ask a man you like!

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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21 thoughts on “Five useful questions to ask a man you like!

  1. Phyllis said:

    Great issues and feedback! People in their 60s have some of the same problems. Thanks for all the tips! If one lets another take them for granted, it is a shame but also an emotional hurt! Good luck to us all!

  2. Frances said:

    Hey James, I’ve been reading your advice for the past five months, but still am quite confused about my relationship with a married man. He is a great guy and I realize he loves his wife, but he also wants “something on the side”. Sometimes he is wonderful and texts, calls, and sees me; other times, he “cannot” get away. I understand that, but it hurts to know that I will always be 2nd in his life. I know that loving a married man is not the best relationship and that I should end it; but I love him. I’m continually confused by his actions and words. Help.

  3. VanessaChiunda said:

    Hie James…😀
    I’ve been a fan of yours for over a year to two now… Always read your ever so helpful articles.
    But I’d really have a bit of weight lifted off of me if….I could please get a direct answer from you??

    My issue is that….I’ve been with this guy since 2014 till present. He was a kind, sweet., innocent looking dedicated church goer…kkkkk…….ya!!! We’ve had our share of breakups n makeups… solely because. ….He cheated on me once in 2015…. Then after that….It was issues with one girl n the next. It’s. …Actually a list of girls….More than 6 I believe….others I’ve personally confronted…others…Still remain a mystery.

    From this…I saw…A side to him that wasn’t there before… acting cocky…Being jumpy, placing 10 character entry passwords on his phone…n no….I’m nt exaggerating. He’d. ….Go out more than usual…. Always on the phone….n if I ask…he’d always claim to hv bn talking to his mom, sister or dad.

    Sometime last year. ..He cheated on me again when he out of town for work… n I found out because. …..theReally were traces of erased naked pictures of a girl n his phone… sexual texts messages about him missing her lips and thighs… TMI….I apologise but…I have to let it out.
    Then…found a replicated picture of him n her holding hands….like that of which him n I had years back. I asked him who it was…He just grinned at me. A while later. …I got him to confess…But. ..It wasn’t much of a confession…But a cocky admission.

    I broke up with him for some months…. I just wanted to move on n be happy. But he came back again promising to change. And for a while he did. I was hesitant about getting back….Until. …He started reaching out to one of those girls again. This time…His excuse was…He thought I was up to something. …so he did it because of that feeling n promised to stop again.

    I got tired of the routine….But. …I really truly am inlove with him….deeply.!!!!!!! But from time to time…He disrespectsays me…talks down on me….Is possessive….talks to me when he feels like it…..

    We…talked…ALOT! He promised alot. N…. Now. ..I’m in China…I left home for school here. But he promised he’d stay with me…That he wouldn’t cheat n would be faithful….. Sadly my heart n soul aren’t comfortable. ..I’m faithful to him…turned down guys because I love him…. Being all celibate n loyal. But…part of me thinks he won’t change. I lostrich all trust in him. ALL!!!!! But….I pray n ask for hope that maybe he’s the one…

    Lately….He’s been upset because I doubt every move he makes. I’m always thinking he’s up to something and I sound like a crazy person at times…n it passes him off.. Last night he cussed me out because of it.

    Do you honestly think he’s right for me????

  4. Laura said:

    As always. Great advise. Great ideas. If only I knew about you when I was younger. I used to avoid parties. I look forward to them now at 61. 😉

  5. Anna said:

    This was extremely useful as always. You are severely talented. THANK YOU!

  6. Amanda said:

    Hi James, I love reading your blogs and all the comments your fans leave for you. Maybe you can be of a little more help to me and anyone else who will be reading this. Advice is always welcome. I’ve been seeing someone for a year now and I enjoy the time we spend together. He seems to enjoy it as well, but when it starts to become more frequent or serious he pulls away for two to three weeks at a time. It’s almost a predictable pattern we have going on. He says he doesn’t want anything serious until his daughter is older. Who he has full custody of and has been heart broke over past relationships that didn’t work out. I completely understand this. But the last month or so he’s been inviting me over while she’s home and coming for dinner to my home and allowing her and I time together. I have loved this, until he still brings up that he doesn’t want a serious relationship. I’m confused. Just today he had an exciting thing happen and text me on his lunch hr to share it with me. Like a kid on Christmas morning! Then when he got home from work invited me over to share again. I know I mean something to him more than just friendship. Pull me in and push me away, that’s what he does. I just keep in mind one of your blogs that you wrote about the strongest trees have the deepest roots and that takes time. Should I be patient with him and see where we can go? Oh yeah, he lives three houses down.
    Thank you

    • James Bauer said:

      Hey Amanda. It sounds like you’ve got a man who is crazy about you.

      His emotional desire is to welcome you into his world. As a result, he slips up on his resolve to put his daughter first.

      But if you think about it, that’s the kind of man you ultimately want to end up with. Someone who is willing to sacrifice what he wants for the well-being of the people he is committed to in his life.

      In this case, he believes it is in his daughter’s best interest if he makes no promises and avoids creating the appearance of a lasting shift in his relationship world. That will change in time, especially as his daughter grows to understand the complexity of adult relationships.

      If there’s any one thing you might want to try (besides waiting), it might be an open discussion of expectations. What does he expect would need to be in place (for himself, for his daughter, or for his relationship with you) before his opinion would switch so that the wise decision is now to move forward with you? Have an open discussion about that topic. Try to be as nonthreatening as possible by treating it like an exploration of possibilities rather than as an attempt to get him to promise something about the future.


  7. Theresa said:

    Hi James, I’m dating this guy and every time we see each other he always say why I’m so nice to him. I’m puzzled is there any fishy going on?

    • James Bauer said:

      It sounds like he’s either fishing for a compliment (e.g. “Because you’re such a wonderful guy!) or trying to give you a genuine compliment (that you make him feel good because of the way you treat him). Either way, it seems he’s trying to invest in his relationship with you, which is a good thing.

  8. Monica said:

    Hi James, I am in a similar situation as Sue above, the difference is, I am married to this man that has gone back to his ex-wife three times in the past almost two years we’ve been together. The last time they were together for two months, he claims they had no intimacy or sex, he just felt “at peace” in her environment…he came back to me because “finally” he realized he love me and with her is just the caring feelings of an exhusband…he seems manipulative to me and is a total selfish woman in the sense of she doesn’t let go of him and she thinks I am not worth it for him, she always appeals to his guilt feeling of how bad she is hurt because of their divorce two years ago…it seems to me that even though he says he loves me, there is no easy way for him to break free from her or at least put concise boundaries for her to understand and respect the fact that he is married now and I the wife not her…your thoughts please?

    • James Bauer said:

      Hi, Monica. The issues here are a little more in-depth and would probably be better addressed through our private coaching service than in a back-and-forth on a blog. Click here to clarify your question and submit it to one of our relationship coaches

  9. SUE said:

    My boyfriend of three years has gone back to his Ex three times.The littest argument he is calling her 6 times a day.He has been with her a month and a half, now calling me again wanting me to see him.He spent seven months with her last time seing me on the side.Will not seem to let her go.Can not live like this any more.Please give me your view on this.He says there is nothing going on between him and her

    • James Bauer said:

      Sue, Rather than asking for opinions about his behavior, I suggest you ask yourself a different question: “Does this man make me happy? Is he the sort of man I want to devote my life to given his lack of fidelity and persistence?”

    • Kari Castano said:

      I know you don’t know me or I you, but my question is why do you keep allowing him back into your life? He says there is nothing going on yet he has gone back 3 times…… YOU deserve better! Everytime you take him back is another missed opportunity with someone else…..possibly the right someone else.

      **Fool me once, shame on you. Fool me twice, shame on me.
      **Strike 3, he is out!
      **If you always do what you’ve always done; you’ll always get what you’ve always gotten.

      You say he will not let her go, I bet she is saying the same about you. This man is clearly playing both of you and you are allowing it every time you see him AND you say you can’t live like this anymore. The choice is yours. Your taking him back tells him this behavior is ok with you and that no matter what you say; you will put up with it. STOP! MOVE ON and find someone worthy of your time.

  10. bernadette said:

    I am forever a student of life and you are an effective teacher. Thanks for your useful and practical information that is tangible, useful and effective. These are wonderfully connecting questions and gives a chance for a person to become open with another, and that can make someones day!

  11. What excellent non-invasive questions, James. Thank you for these ideas which will surely work even if one is in a long-term relationship. They just need to be adapted a bit to suit the circumstances. Questions 2 and 4 are really brilliant! Can’t wait to try them out.

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