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i have a guy friend who is really skinny. He's got long hair and the most amazing eyes. He can also be a bit of a stick in the mud especially with parties and stuff. I think it'd be a blast to dress him up as a girl for Halloween. He'd look amazing! How do I bring this up besides saying you'd look great as a girl. My friends think it'd be a great costume too. I thought of maybe trying to win a bet with him or trick him somehow so I didn't have to just say "Hey I want to put you in a dress". How do I bring this up?

2006-10-18 01:38:08 · 9 answers · asked by Heather M 1 in Beauty & Style Fashion & Accessories

9 answers

I think the bet idea is a good one...or mayb if u dress up as a boy then you guys would go as a regulr couple but with a different sex than usual...that would be a good idea

2006-10-18 01:41:58 · answer #1 · answered by M.J. 2 · 1 1

Start off by talking about Halloween, and what your both going to dress as. See if he already has an idea. If not, Tell him that you'd bet you could make him look good as a girl. And that the costume would be some what in expensive. If he's not thrilled about it, suggest that you try it at home one evening prior to Halloween, "Just to see what it would look like." If he has an idea of a costume already, Listen to it, then say something like Well, that's not a bad Idea, But, I think you'd look better if I dressed you as a girl. Then again suggest that you try it prior to Halloween to see how it looks. Then tell him that if he likes the way he looks, then he can do that, but if not, He can still go as his original idea. That's how my ex talked me into it. And now I dress regularly. Also, an idea for you. Take four round balloons, Stuff one inside of another so there doubled up. Lightly fill the inside balloons with water, Tie them, then tie the outside balloon. keeping the knots one under the other. Put them in his bra, They'll move naturally, and the knots will look like nipples.

2006-10-18 08:55:01 · answer #2 · answered by electronvette02 2 · 0 0

Don't try to trick him. You risk hurting him and your friendship when you're dishonest.

Start a conversation about Halloween. Ask him what he's going as. If he already has a costume, then forget about it. If he doesn't than make your suggestion.
"I think it would be really funny if you dressed up like a girl."
DO NOT mention how great you think he would look as a girl. That will only upset him, and he'll never consider doing it. Make it more of a joke, and point out the irony.

If neither of you have bought a costume yet, offer him a deal.
"Since neither of us knows what we are going as, how about you get to pick my costume, and I'll pick yours."
Then be willing to suffer with whatever he picks for you, no matter how embarrassing it is. It can't be worse than you dressing him as a guy.

2006-10-18 09:43:43 · answer #3 · answered by welches_grape_jelly 6 · 1 0

I think it could potentially make him doubt his masculinity, maybe you should let him decide his own costume. If he is hesitant about going to parties, I am sure he will be less inclined to go dressed up as a girl.

2006-10-18 09:02:43 · answer #4 · answered by j_sanchez2109 2 · 0 0

If he is secure with his manhood it should not be a problem, maybe you should tell him how it will be funny to see such a Verile guy like a girl, it will be a hoot.. and besides if he likes you he will do anything for you.

2006-10-18 08:46:24 · answer #5 · answered by Anonymous · 1 0

Y not go for exchange costume whereby girls wear guys clothes n guys wear girls clothes.. if it is hard then i suggest u play a game with him.. a game tat guys wear girls stuff hahaz.. or perhaps truth or dare game if u heard such things b4...

2006-10-18 08:48:06 · answer #6 · answered by Mighty 2 · 0 1

Just ask him, I wish my better half would ask me to dress up for Halloween.

2006-10-18 12:46:44 · answer #7 · answered by Nascar 5 · 1 0

force him

2006-10-19 02:15:02 · answer #8 · answered by john 7 · 0 0

ridiculous-you, i mean

2006-10-18 08:45:06 · answer #9 · answered by Anonymous · 0 1

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