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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