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Groom 101

26 Bachelor Party Challenges

Chris Easter

As best man, your job is to plan and execute a bachelor party that will give your buddy a proper send-off into married life. If you’re planning to hit the bars, casinos or strip clubs – it’s never a bad idea to have a list of challenges or games for the groom-to-be to complete during the course of the night. If properly planned, these games can turn into some hilarious moments that won’t soon be forgotten.

First off, it’s always a good idea to have the groom-to-be wear some type of ridiculous T-shirt or hat that designates it’s his bachelor party. A lot of best men like to get creative and come up with their own T-shirt design, which we definitely recommend. Remember, don’t hold anything back. Be as obscene as necessary.

As for the challenges, here are 26 options to help you get started.

  1. The groom must get 50 women to sign his shirt.
  2. Stuff a fanny pack full of embarrassing random items. Make the groom wear it around all night until he’s given all of the bag’s contents to women.
  3. Find a girl with the same name as his fiancée and buy her a drink.
  4. Find 10 girls who smoke and offer each of them a light.
  5. Get the best man’s phone number into 10 random girls’ phones.
  6. Get a woman’s bra.
  7. Get a woman’s underwear.
  8. Get a condom from a woman.
  9. Get a woman’s phone number.
  10. Find a bachelorette and dance with her.
  11. Do a body shot off of a woman.
  12. Have a woman do a body shot off of the groom.
  13. Make the groom carry an inflatable doll around all night. (extra points if the doll is male)
  14. The groom has to get a blonde, a brunette and a red-head to each buy him a drink.
  15. Serenade an unsuspecting girl with a love song.
  16. Make the groom wear a ball and chain around all night.
  17. For every beer or drink the groom gets, make him ask for a girl’s phone number. Every time he gets shot down, he has to take a shot.
  18. Find a woman who can tie a cherry stem into a knot with her tongue. Make her prove it and then buy her a drink.
  19. Have the groom find a girl with really bright lipstick to kiss his cheek. Don’t let him wash it off all night.
  20. Have a girl do a naughty dance move for the groom for a drink or beads.
  21. Get two girls to kiss each other in honor of the groom’s upcoming nuptials.
  22. Convince a stranger that your bride is still a virgin.
  23. Convince a girl to rub the best man’s shoulders.
  24. Try to convince a woman that women should remain virgins until marriage and that men should not have to.

Remember to keep score to see how many the groom-to-be completed. Here’s the official TMR scoring breakdown:
0-5: Is he already married?
6-12: Maybe a couple more years of bachelorhood wouldn’t be a bad thing.
13-20: Time to cut off the booze.
21-26: Maybe marriage isn’t the best idea for this guy.

TMR Recommendation: Remember that these challenges are all in good fun. If you see your buddy about to do something stupid, step in and make sure he doesn’t cause the wedding to get canceled!

Have your own bachelor party games or challenges? Drop us a line. We’d love to hear what you’ve got.

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One Comment

  • Kara Fraser 1 month ago

    Some great (and some risky) challenges in there, hats off if he can find a woman who can make the cherry knot! Cool article 🙂

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