8 Tricks to Make Your Boring Date Interesting

Have you ever been on a date where the person was so boring that you would rather be at home watching paint dry? I think we all have, and most of us don’t want to just take off right away, we’re not jerks, right!?

Dealing with bad dates is practically my autobiography and over the years I have had some pretty painful experiences. One boring date after another date has forced me to find tricks to help adapt to these yawn filled situation, enhance them you might say. These tricks not only help add some needed amusement to your night but also help to make sure the hour it took it to get ready and the 45-minute Uber ride wasn’t all for nothing!

Happy Birthday, Surprise!?

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Who doesn’t love to be a little facetious on a date? For this trick, you will need to wait for your date to go to the toilet.  Once they are securely preoccupied in the porcelain place, wave down your waiter and tell them it’s your date’s birthday. 15 minutes later when the servers arrive with cake and song, it will embarrassingly catch your date off guard putting them into a state of “WTF just happened?”  Trust me, you won’t forget how big of a smile it brought to your face. Their face?!  Well, they should laugh. If they don’t, you probably should help them pull the stick out of their butt.

Play to Their

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By playing to their personality you can make the date much more entertaining and also bring the most out of that person.  If they are quite funny, keep them drinking! They will shortly become hilarious. If they are
overly egotistic, try to push their buttons. Say things that get under their skin so they throw a tantrum. Or if they are just seriously good-looking, shut the hell up! Have them tell you a long story so you can just stare and nod. Stare and nod my friends.

Talk About Travel

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If your date seems to be characterless when speaking,  get them to talk about travel. Whether it was their time in Peru or a week getaway in the country to their Aunt Sherman’s,  redirect the conversation to accommodate this topic. A lifeless date will come alive in seconds when they start talking about a holiday or crazy adventure. With any luck they will be able to maintain that energy throughout the rest of the date, drastically improving your odds of not wanting stabbing yourself in the foot.


  I am a big advocate that chocolate cures everything. Bad day? Chocolate! Bad fight? Chocolate! So when you are on a bad date? Chocolate chocolate chocolate! I don’t care if you are just grabbing a drink or having a big night out. Order a dessert before your main,  drink a chocolate martini or go to the bathroom and do a line of cacao for goodness sakes! Indulging chocolate will raise your serotonin levels which will allow for a more pleasurable experience or, at the minimum you will get a proper sugar high?

Do Something!

If you have run out of tricks to make conversation intriguing, then it is time to get up and do something. Go laser tagging where you literally can run away from them. Go bowling where it is too loud to hear them complain about some coworker.  Or my personal favorite, take them to a strip club where they actually physically and mentally become disabled.  Just do something where little to no talking is required and you can still manage to squeeze some fun out of the night.

 Get Social

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Whether it is the people sitting next to you at the restaurant or a group to your left at the bar, get socializing so you are not alone. It’s simple math, the more personalities included on your date the better the odds of someone actually being interesting. The more friends the better because who knows, maybe that curious stare from your left will tickle your fancy a different night?

 Get Drunk 

Ahhhhh alcohol, the universal medicinal beverage that can help even make reading tax law fun. It is no secret the more you drink the more interesting a night becomes and being stuck on a craphole of a date is no exception. Keep shovelling those drinks down until their company turns pleasurable.  You might as well keep on going until they become hot, right? Or you can really toss then down until you wake up that next morning with absolutely no recollection of the date! Because the number 1 way to fix a boring date is too completely forget that it ever even happened 🙂

So there you go! Hopefully, a few of these can help you get through your next bad date.  I usually use a combination of a few to make sure no night of mine ever goes to waste. 

What tricks do you use?

glass of whiskey, making your date more fun

<3 Hot Mess


  1. The egotist thing made me smile – it’s not working with Trump, is it – he just becomes an even bigger asshole 🙂

  2. OMG, don’t you dare start digging up my old memories! You’ve got to be creative for certain!

  3. Haha these are great! I love the birthday idea that would definitely give you something to laugh and talk about.

  4. These are interesting. Thanks for posting.

  5. Hahahahaha these were hilarious and an interesting read! Thanks for brightening my day!

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