relationship promblems

Questions To Ask To Keep the Convo Fresh on the First Date

To My Fellas,

I’ve been there before, a few times actually, just like you all have or probably will.  It’s the crucially important first date where you’re trying your best to keep the lady you’re into mentally and intellectually stimulated.  After all, first impressions are everything, and you want to establish to the lady you’re with you’re definitely the type of man who can intrigue her and hold her attention. 

There you are doing all you can to ensure there is never a moment of awkward silence between the 2 of you, because we as men understand any awkward silence could be the death knell of any kind of potentially intimate connection we could have had with the women we’re feeling.  You could be the most interesting and upstanding guy in the world, but we understand that how effectively articulate and display what you’re about is all that matters in dating and that, whether it’s fair or not, women see a man taking huge gaps in conversation as a sign of a lack of confidence and of knowledge in a man even when she, herself, isn’t talking about anything intriguing herself.  

I know how mounting the pressure can be to be expected to keep up a riveting conversation for–sometimes–hours on end.  Like I said, though, whether it’s fair or not, you’re still expected to be the conversational thought leader on the first date by women.  You’re expected to articulate key points about your overall personality, you’re expected to make the woman comfortable by keeping the verbal exchange lighthearted and humorous while at the same time mature and intelligent, and you’re expected to know just what kind of strategic questions to ask that make her feel comfortable so she’ll open up about just what kind of attributes comprise her.  

It is what it is, fellas.  Read ’em and weep.  However, not to worry.  Your relationship adviser is on the job, and, just in case you happen to run out of things to talk about on the first date, I’ve devised a few of questions I’ve found to be useful in resuscitating any verbal exchange that’s gone cold or to help change the subject and divert attention away from anything you said because you were nervous.  Heaven knows we’ve all asked a woman “How you doing today” only for her to say, “I’m fine, but you already asked me that.”

That said, I, myself, have mastered the art of conversation with women, and I wanted to lend a few questions I like to ask in order to keep the dialogue flowing smoothly between a lady and I.  Feel free to incorporate them in your conversational repertoire when you’re on the first date with the lady you’re trying to spark some fireworks with.  

By the way, I’m not advocating for you to just use these questions and statements and to not think of and use your own.  At the end of the day, this is the woman you plan on being with, so you’d better have an understanding of what you really want and how to question a lady to find out if she exhibits those qualities.

Whether or not you form a connection with the lady you’re in the company of is entirely dependent on the romance your own unique conversation forges.  These questions are merely lifelines just in case the romantic discussion you’re trying to formulate falls flat and you need a new topic to rekindle the zest of the dialogue you’ve already begun to establish on your own.

Feel free to let me know if you do or don’t have success with these, fellas.  I would love to hear your feedback.  

By the way, don’t be afraid to ask follow-up questions as the person you’re with answers what you are asking.  If you’re curious about something she says, man up and ask her to elaborate on it.  Women are attracted to a man who wants to know more about that personality and how their mind works, in-depth.  So, don’t solely rely on these questions to keep your conversation vibrant.  They are just ways for you to stoke the chemistry between you and the lady aflame:  

  1. What are your biggest pet peeves (so that you’ll know never to do them/also tell them what yours are in response)?

  2. How long have you lived in the area long, and, if you’re not native to here, what brought you out to this side of town?

  3. What was it like where you grew up?

  4. What are you passionate about and life, and how have you pursued that passion or those passions?

  5. What types of things do you value in a relationship?

  6. What kinds of things do you feel you could bring to a relationship that are of value to a man’s life?

  7. What was a really thought-provoking book your read or movie you’ve watched lately, and why did it resonate with you?

  8. Do you feel your parents are a healthy example of how a relationship should properly function?

  9. Is there any place you’ve always wanted to live in, and why?

  10. Why kind of characteristics do you value in a man, and do I exhibit any of those characteristics so far (if she says “no,” don’t take it personally and brush it off and keep it moving).

  11. Are there Any hotspots you and your friends like to hang out at in the city?

  12. Are there any long term goals you’re focusing on in life right now?

  13. What is your favorite part about *where ever it is you live*? 

  14. Do you feel like you’ve reached the height of your profession at this point in your life (be ready to have that same question asked back to you by the way)? 

  15. What is your favorite food (Fellas, if you know how to make the meal she names, trust me when I say it’ll get your foot all the way in the door)?

  16. What are the main things that attract you to man, and have I exhibited any of those attributes?

  17. What is your idea of a perfect night out on the town?

  18. What is the most pressing question you have to ask a man like me?

  19. How are you enjoying this evening?  Because, I wouldn’t want to spend my evening any other way than spending it here in your presence.  

  20. Do you have any big plans for this upcoming weekend (Take this as an opportunity to plan a second date if you are available)?

  21. On a scale of 1 to 5, with 5 being the highest, how who you rate how high your quality is as a female, and why would you give yourself that score? 

  22. Thus far, are there any things I’ve displayed that you find desirable about me?


From the Soul,  


Hello Family,

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