Wise Guys: How Can I Get Him to Dress Up for Halloween?

Advice from three of our guy friends. This week they answer the following: “What’s the best way to get your boyfriend/husband to dress up for Halloween with you, especially if he’s reluctant?” To ask the guys your own question, click here.

anonymous_suitStraight Married Guy (Matt): I’ve read about women in NYC who trade blowjobs for their partners’ closet space. I’m sure there’s a blowjob-to-costume ratio here that would leave both sides feeling happy with the arrangement. Part of me hates this idea, and feels like blowjobs (like flowers) ought to be given just because, and not used as some sort of bargaining chip. The same goes for wearing a costume. She wants a fun night out on Halloween — is it really that hard to put the tiniest bit of effort into a costume? Maybe the simplest answer is a post-party reward that’s more mutually gratifying, like telling him you want to have his Mark Antony take your Cleopatra at the end of the night. This probably limits the costume choices somewhat, in that sex is not going to sound nearly as appealing if you’re dressed as a zombie or Fozzie Bear or Raggedy Ann or whatever. Still, as a fallback, he’d probably gladly take a blowjob from any of them.

terence_100Gay Committed Guy (Terence): Halloween dress-up is tricky business since some guys hate it or think it’s wanky. Look, the absolute best thing you can do is choose a costume that is cool. I know this is completely subjective, but you should know your man better than anyone. By cool I also mean the costume should be 100% not 75% or 80%, but absolutely 100% with all accessories. If it’s a cowboy, you need a real hat, good boots, awesome chaps, cowboy shirt and rope. Half-assed doesn’t cut it on Halloween. Not that I think cowboy costumes are all that cool. I’d think an astronaut costume with a badass helmet and some lights inside would be cool.

Straight Single Guy (Tom Miller): I feel bad for guys who don’t like costume parties — lighten up, homes. Step one is to get a costume that he’ll think makes him look cool, is comfortable in, and his friends will recognize and appreciate (like the Dude from The Big Lebowski). Drinks and a steady barrage of compliments will help. If he doesn’t bite, remember that relationships are a give-and-take operation and you may have to trade for something you’re not thrilled about. If he’s still being a big GD baby about the whole thing, give up. It’s not worth a grudge. If you’re not above being conniving, let him know that you may costume partner with someone else.

Our “guys” are a rotating group of contributors. Tom Miller writes the Tomfoolery blog for YourTango; Terence is an American living in Sydney; Matt is a little shy. To ask the guys your own question, click here.


  1. I’d say the hair-dye scooby doo shirt counts, Mml. L. Though not a costume, when paired with his willingness to attend a party with you, it constitutes a good-faith effort to do something with you that you think is fun. That’s the most anyone can ask for, I think!

  2. @figleaf: that’s a great idea — mind if i steal it? my girlfriend loves dressing up, and i don’t mind so long as it’s simple and funny, but it’s all of my friends who are sticks in the mud when it comes to halloween. every year i’m dressed at the party while the people i hang with are just dressed in their normal attire.
    with an idea like yours, i think they may be swayed…

  3. One suggestion for a group prize that actually might work if it’s really that common for men not to want to dress up for a Halloween party:

    Tell them to pick up a yellow blazer and a dumb white hat at Goodwill, and a pair of sunglasses. Hand them one of those steno notebooks with the wires across the top. Hand them a marker. Tell them to write the numbers 1 – 10 in really big writing on the first ten pages of the steno pad.

    Tell all your girlfriends to do the same. Then at the party you line them all up in chairs along the wall near the entrance, hand them all drinks, and voila — instant Olympic Judging Committee group costume.

    The downside is that they might actually start judging people’s costumes. The upside is they’d look really cute in a doofy sort of way.


  4. Nah, My Man doesn’t usually dress up for Halloween. He may put on his Scooby Doo T Shirt (it glows in the dark) or spray paint his hair bright colors, but he won’t do a costume.

    I’m going to be a cop this year, and I’d love him to dress up in either an orange jump suit or a black and white stripe prisoner uniform with in handcuffs. He won’t do it. I’m willing to bet he’ll get a blow job anyway. I’m just nice that way.


  5. ^ And by the way… blowjobs in exchange for compliance? Come on. First of all, if a woman were to haggle with me using sex, she’d have to go way farther than a BJ, as oral is de rigeur in my boudoir. It’d have to be a threesome – the MFF kind, mind you -or the butt.

    But in general I’m not a fan of trades-off or negotiating in relationships. The flip-side of offering someone a nicety for compliance, is denying them one for non-compliance.

    My girlfriend can do whatever she wants. If I’m ok with her choices I’ll stay with her. If I’m not I’ll leave her. I expect to be treated the same way. If I say I don’t want to wear a costume, I don’t want to wear a damn costume. Don’t pester me.

    Incidentally, I think it’s a little lame to refuse to wear a costume…

  6. Fun times with your partner happen either when they’re equally psyched, or at least willing to indulge you AND BE A GOOD SPORT ABOUT IT.

    Dragging someone along who doesn’t want to be there is never fun – “OK, FINE, I’ll wear a costume. Stupid halloween…”

    I’m always comfortable leaving my partner out if she’s determined to be a stick-in-the-mud. I’d much rather not fight and just leave her home than twist her arm into something she doesn’t want to do.

    Leave the grouch on his couch. Call your girls, dress up in crazy costumes, and go have a blast.

    …aaaaaaahhh, who am I kidding. If you’re like most people, you’d rather fight with your partner about it and let it ruin the night for both of you.

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