113 Naughty and Nice Conversation Starters

The secret to the perfect date is in the CONVERSATION...
Without good conversation, the date may as well be over.


Our naughty conversation starters are made to push boundaries.

A WARNING: The questions in this list may not be questions that you want to know the answers to, or take action upon - some fantasies should remain a fantasy... whatever happens beyond the conversation is up to you and your date.

51 NAUGHTY Conversation Starters

Download your list of saucy conversation starters.

WARNING: this is not for all couples!

We cannot stress enough, the NAUGHTY CONVERSTION starters are not only hot, but cover topics of conversation that is not suited to ALL couples.

5 Questions You'll Find Inside the NAUGHTY CONVERSATION STARTERS - try these questions tonight

  • Has anyone ever caught you naked by
    accident? Tell me the story.
  • Imagine I've blindfolded you. What should
    I do next?
  • If I went down on you while you were
    driving the car, do you think you could
    handle it?
  • What sex toy have you always wanted to
  • If I was going to buy new lingerie, what
    should I buy?
  • What's your biggest turn on right now?
  $7.99 Naughty! (BUY ME)

62 NICE Conversation Starters

Here, you'll find nice, fun conversation starters

For couples who like to be good.

Highly recommended for couples who want to have a sweet time with their lover.

5 Questions You'll Find Inside the NICE CONVERSATION STARTERS - try these questions tonight

  • If you found $10,000 in the street what
    would you do with it?
  • If I could time travel, I'd go...
  • The best thing I've ever won is…
  • One thing we should do more of is...
  • If you could have dinner with any three
    people, dead or alive, who would they be? And why?
  • Who is the best teacher you've ever had?
  $2.99 Nice (buy me)

We ask $30 Date Night co-founder a few personal questions

This video is unscripted. Creator of $30 Date Night, Denis Merkas answers questions exactly as he would have if he was out on a date with Emma.

Denis and Emma have been married since 2009 and had dated for years before that. Even after all this time, Emma learned something about Denis she never known about before...
This is exactly what conversation starters do.


Ask questions that spark conversations. Simple, right? We bet there are still lots of things you didn't know about your sweetie.


Simple questions that attract interesting answers. The more you probe, the more you learn. Totally fun!

Great Conversation

You'll learn things you never knew about your date before, no matter how long you've been together! We guarantee it..


  • Don't force answers: Your date has the right to skip questions if they wish, without explanation. Please respect this rule, it will save your date night and maybe your relationship.
  • If you're uncomfortable asking a question you can definitely skip it. Some questions may not be suited to your relationship, or even just to that moment in time. Skip it.
  • Elaborate and discuss: One-worded answers are boring, there's a story behind every question. If you want to probe further you should, but remember the first rule. If the conversation is flowing, don't interrupt to ask the next question! Just let it flow. If you're talking animatedly, you're doing it right! Keep the rest of the questions for another time!
  • Take it in turns to ask the questions: You can go one after the other, or tear the page in half, or make two copies and fold the page in half... whatever works.

This could be the best sex you've ever had!


Emma and I are open-minded, there isn't much that will shock or embarrass either of us. But the Naughty Conversation starters had me bound up, on my back foot and at times, speechless! With that said, it made for one amazing night out. We laughed, we blushed and we covered topics that I thought I'd never discuss with my wife, and all over a lovely dinner in a busy restaurant. The conversation was so hot that I kept looking around the room to see what ears were eavesdropping in.

We covered about half of the questions over dinner - that was enough to give us a good 90 minutes of solid entertainment. It was a wild ride of emotions, there was so much discussion around sex that it made for a pretty exciting dinner and had us both revved up by the time dinner ended... so much so, we jumped each other as soon as we got in the front door!


No peeking at the questions! Keep it a surprise for both you and your date. Once you've downloaded the Conversation Starters, open the file and print off two copies immediately. DO NOT LOOK AT THE QUESTIONS, You'll spoil the fun. Fold both pages in half and seal them in an envelope, ready for when you go out on date night. You'll LOSE the intensity if you peek at the questions before the date.

Creators of $30 Date Night: Emma and Denis Merkas