First Date? Here’s a Tip: Don’t Be Boring!

First Date Conversation Tips

You know it.

I know it. Of all the first date mistakes one can make, this one could spell disaster… Being BORING!

Yep, coming across as a bore (or rather, sharing boring conversation) is like the kiss of death on any first date. I talk about this in Girl Gets Ring as well, but the main premise is this…

…on a first date You have the ability to direct the flow of conversation and keep things interesting. So use that ability to your advantage.

It’s like with sales.

You (usually) only have one chance to really wow someone and make a great first impression. Same goes for a first date.

First Date Mistakes Are Costly…

You get one chance to really connect and light a fire between you and a man… and it usually starts with your first date. Your conversation on the first date absolutely cannot suck if you want it to lead to a second date and to get more opportunities to spend time together.

You (and your date) could be the most fascinating, scintillating, adventurous two people on the planet, two people that go on amazing excursions every other week, two people that are absolutely a match made in heaven

But if you come across as boring on a first date, both of you wind up walking away scratching your heads, wondering where that initial spark went.

It’s almost like you forgot just how awesome you are and relegated your first date conversation to safe boring stuff because you thought that’s what you’re supposed to do… and as a result your awesomeness was missed altogether!


You MUST Avoid Boring Conversation!

Boring conversation on a first date is a big dating fail, just so you know.

I don’t mean to be harsh here, but I see it all the time. Men and women whose conversations read more like a resume than an occasion for evocative discovery and deep connection.

Men and women that discuss totally uninteresting things in a misguided attempt to get to know each other, and then walk away from the date saying “Man… that had to have been the worst first date ever… I can’t believe I thought they were so hot!”

Sound remotely familiar? I’m betting it does.

The key thing you have to remember is this… you hold power with your words. Your words can be the crowbar that jacks open his trunk, exposing all his goodies to the world.

Do you really want to look in that trunk and find his stats? Or do you want to look in that trunk and find him?

How To Make a Great First Impression

If you’re looking for a long-term love, you need to get to know him not just know about him.

Ask questions that make him think. Ask questions that make him talk and open up. Ask questions that make him recognize you are different from the average girl.

You’re not just another Saturday night date, you are the best date he can remember having.


Because you are asking him things that make an impact on him, that aren’t the typical conversation starters he was probably expecting. You have thrown him off balance and guess what?

He likes it!

It doesn’t take much to make a great first impression on someone. But you can’t just leave it up to your date to take the lead.

Sometimes they won’t and it’s nothing to do with how interesting they are, but more to do with their own conversation skills.

Of course it takes two to make great conversation but there’s no rule book saying you can’t kick things off yourself.

And if you kick things off and it spirals from there… awesome, mission accomplished.

If you kick things off and the date still falls flat… well now you know and can make the decision to try harder or move on to more exciting pastures.

Conversation Tips That Make For a Great First Date:

Ask open-ended questions that require more than a yes or no response.

First Date Tip #1…

Lead the conversation with slightly off-beat questions, like these:

  • “What was your favorite game to play as a child and why?”
  • “What’s the hands-down best way to make you smile when you’re having a bad day?”
  • “Who is your favorite person on the planet and why?”
  • “What’s your favorite color and when did you realize it was your favorite color?”
  • “What’s the worst habit of yours that you can think of in 3 seconds or less? GO!”

First Date Tip #2…

Make the conversation Interesting with thought provoking questions, like:

  • “Tell me a story of a time you were the happiest you can ever remember being.”
  • “Tell me something funny about growing up in your family.”
  • “Tell me the biggest quirk about your Mom and/or Dad that they’ve passed on to you.”
  • “Name me three of your absolute favorite places to go/things to eat/books to read in 10 seconds or less. Go!”

As you can see, sparking interesting conversation doesn’t take a science degree, simply a little forethought.

You have to move beyond the typical “What do you do for a living?” type questions and focus on drawing forth information that really tells you something about the man you are with.

Not only will it intrigue you into getting to know him further, it will make you seem extremely exciting and interesting to him as well.

Us guys call that a first date slam dunk.

(OK maybe we don’t do that.) 😉

Regardless I’d love to hear your own first date stories in the comments below. Over to you!

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Leave A Reply (9 comments so far)

  1. Ms Almost Right
    7 years ago

    WOW! Talk about thought provoking…what if Mr Almost Right gets ‘stumped’ as I just did whilst asking myself those same questions…pregnant pause…most uncomfortable, to say the least.8-( Personally, I would have to have an answer up my sleeve, just in case he asks me to go first. Better still…how would he handle a situation like that. The mind boggles! 😎

  2. p lexy
    7 years ago

    First date conversation

    I knew I d just blown it. There was this guy that had been after me for a while and when we finally went on a date I allowed him do all the questioning and I kept providing all the answers like a robot without extracting any information from. I just knew I’d screwed up. He had not called since then. Thanks 4 dis. Am never gonna be a boring date ever again

  3. sue
    7 years ago

    my guy will love these questions. i asked him one yesterday similar to these and he doesn’t know the answer and says he needs time to think about it and that no-one has ever asked him that before. he is definetely intrigued : )

  4. Sally
    6 years ago

    I still remember my first date as if it was yesterday, I have met this guy on line and we did get along so well and after two months of charting he asked for my work address and I gave it to him. so one day I was at work and he just came unannounced and he said he came just to take me out for lunch…I was so shocked and stressed because I didn’t expect it but you know what? everything went very well because I was my self. I didn’t try to be someone am not, I was so funny, flirty, passing jokes and laughing my lungs out. his a very quite person and very shy too but that day :)) I was on my knees in a middle of a top restaurant laughing, tears running on my face because I manage to make him feel free and comfortable about himself and he liked it a lot…everything just happened naturally and we bonded like crazy – I didn’t worry about what I was wearing or about my hair but I was in the moment enjoying myself and his company. its been 9months now and we are still together and he loves my craziness and we still talk about our first date… just be yourself and the person will enjoy you for who you are as a person!!!

  5. JChristian
    6 years ago

    Aww, Sally. Your story is beyond refreshing. How are things going for you guys now? Are you still dating each other?

    I’m sure many women would be terrified of a man seeing them in their “natural state” — you know, natural hair and makeup, jeans and a t-shirt and whatnot.

    But honestly, that’s what guys want out of a girl. Just someone who is relaxed and who isn’t afraid of being themselves. Isn’t that what we all want? Why fight it and hide it with superficial notions.

    My question for you ladies: what do you all want from men?

    I think I know what women want, but I’m guessing that since I won’t be able to read minds like Mel Gibson does in that movie… I better cut to the chase and ask you guys here.


  6. Shelley
    6 years ago

    I really like the first-date tips… especially with the questions.

    It’s all about having that great first impression. As a journalist I try to ask intelligent, engaging questions all the time. I can be tough, but you have to keep the conversation moving and you have to keep it interesting. That’s what convinces a person you care.

    I started seeing a guy a little over four years ago, and eventually our talks, which started off quiet and awkward broadening to meaningful conversations and lots of fun times out and about.

    That’s why this site is a cool resource. I have a dating site, too, but I just love helping people out. It’s a tough world…. that dating world… and you need to train yourself to master it as best as possible.


  7. Elida
    6 years ago

    great tips, thanks so much!!

  8. Debra Richmond
    6 years ago

    Alright – OMG! You may not even believe me – first of all I’m already 58, was 57 then – my date was 48 (I’ve always dated/been married to younger men, not a cougar, it just happens that way)but anyway, this was my first date since my husband and I had seperated. I had been out a lot and met som guys, but this was my first date where I had allowed a guy to come to my house and pick me up.
    When he arrived, I was almost ready & had him to come in for a second. I thought he had left his truck running because i kept seeing headlights shining in the street, Finally, he opened the door, I turned to lock it, when i tuned around, he had a limo waiting! I couldnt believe it. The driver let me inside. This guy had a dozen roses, any & every sort of liquior I had mentioned that I enjoyed drinking,and a disc made that contained all of my favorite kind of music.
    We drove all over town & had a drink or two, saw a concert, danced,& just stopped into any & every place we wanted to. It was so cool to not have to worry about driving, walking to the car, etc.
    Finally, after everything had closed, we stopped at I-hop & the driver brought out menus & we ordered breakfast & wenty back to my place to eat.
    Yea we were on the couch horsing around, I was so turned on by him, with my clothes on, just my shirt above my head, He mentioned the bedroom, I said, “No”that was fine. He con’t. to act that way for about three months, sending me flowers, ballons, candy, you name it, to the campus where I teach. The principal began announcing each time something arrived!
    WELL, we dated a little over a year. BUT. all the while, I discovered that about every 3-4 months, he was hooking up with a married woman that he had a relationship with prior to me who had been seperated at the time. IT MADE ME PHYSICALLY ILL!
    Six months later, Ive discover your information and, even at my age, I need to figure out what’s up with many of the men today.
    What did I learn from that, men cheat? That wasnt enough – if you read this and are capable of providing me with Any advice, I’d love to hear it!

  9. Monarch
    4 years ago

    Men want a female that can take charge, bring humor, cook, clean, has something to say about current events, shows an interest in him and what in what his interests are at the time.