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Lost Bet - playful ideas for what I should have her do

VictorK

Senior Don Juan
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Hello all,

Here is my situation looking for some suggestions -

1. Met a 24 yr old office intern that's leaving the company in a week. We've kept things casual but have seemed to hit it off. (She baked a pie for my parents anniversary).

2. We've met up once outside of the office for coffee and she texts me on weekends and at night. The conversations are light and she tries to tease me.

3. We placed a friendly wager on something and she lost. The wager says the winner can choose something the loser has to do. So what are some flirty playful ideas I could say? My goal is to ask her out officially once she leaves the company

Thanks for the insights gentlemen
 

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Don Juan
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This is fun, first get a feel of the worst type of dares she has done by asking her. Then ask her if she's ever drivin in her car naked at night. She'll say you're probably crazy, just say it sounds pretty daring and funny in a ****y funny way. Tell her you dare her to drive around in her car butt naked at night around her block. How you witness it is up to you guys to decide, but man this is an awesome idea, if she's a bit into you she'll probably do it. I almost got a chick to do this, then I decided not to persue.
 

Peaks&Valleys

Master Don Juan
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This is actually a date that is thinly disguised as a bet....which can make it kind of fun.

Try to figure out something that she's never done before that you (preferably something you're good at) like to do and vice versa. Then make the bet that the loser has to join in on the winners choice of activity.

What are her interests...what are yours? Does she like to do pottery decorating or some $hit like that? Does she despise anything sports related? And you like to tear up the local ice rink? Rock climbing?

Or if you can't figure out some type of activity then you can go with the old fail safe catch all movie/TV date. If you win she has to join you at the local sports bar for a night of exciting football/hockey, and if she wins you have to go to the movies with her to watch one of those gay a$$ chick flicks she's been dying to see.

Something like that.
 

Scaramouche

Master Don Juan
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Dear Victor,
Playing double dare you!.....now that can be real fun......I had a plate for eighteen months who was a bit of an exhibitionist....we started off by Shagging in car parks,strange,her excitement grew the more frantic,the more likely it was that we were going to be caught out...it generated from this to having fun on mountain peaks,both on a little bivouac mattress I would carry and in her car...we did all the seven peaks around my City...It did become a bit challenging when she got an appetite for svex in the Cinema...One night she was on her knees giving me a head job,in the back row,when out of nowhere a young Usherette Girl came and shone a torch on to us....She just let out a shocked...."Oh!"then said "Sorry!"
...I suppose it had it funny side,but having two daughters myself I felt bad about it for a while.
 

Lexington

Master Don Juan
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Keep it simple. Make her take you out for a night of drinks for which she has to pay. You get her out on a "date", it's free for you and she's investing in you which makes it easier to close the deal.
 
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SecondHalf

Master Don Juan
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Get her out but don't tell her what she has to do. Just keep saying trust me. The anticipation will work its own magic.

What you'll end up doing, who knows, you can think of that later.

SH
 
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