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I vote for serving it after the wedding, with the cupcakes. I like your idea of clear plastic cups, and having people serve themselves. If you're having a *lot* of people, though, the self-serve thing might get kind of hairy.
I'd say it fits well during the cocktail hour, the flavor sounds like it would compliment well!
Are you doing passed apps for the cocktail hour? Or stations? Or buffet style? I think passed sorbet cups could be really nice. Are you providing your own dishes or could your catering company provide something?
Also, I'm curious if you're really serving cupcakes as dinner, or if that was a typo in your first post :)
@daydreamwanderer: No cupcakes are dessert. lol. Cocktail hour is stationary crackers, fruit and cheese. Our drinks are beer, wine, and mojitos. We're having a full dinner.
I may be able to get the catering company to provide glassware but I'm trying to save money. I could use the free ritas ice cups but I thought maybe that would be tacky? ooh I used the "t" word but it was towards myself so don't hate me! lol
What do the free cups look like? Google image please! :)
Will the caterers be willing to scoop it into cups your provide, or will they charge extra since it's not their food? If they'll scoop, it seems least messy to have it pre-scooped, but it doesn't seem worth it to pay a lot for that, since you kind of like the idea of DIY for your guests. :)

I can definitely see it in cups this shape - just one beautiful round scoop in each.
Wow you guys have Rita's down there!? I love the idea of having it at the cocktail hour! But not everyone will love cranberry so maybe have an additional choice. I see your date is in May...maybe a more "springy" fruit flavor or a cream ice?
Sorry for the HUGE image! But they look like this. I think this is the small, kid size cup, which is what I would get. I do think my caterer would charge me to serve it...or bump up the 'service charge'.

@Swiss Miss to Bee: Yeah I don't know if Cranberry is available then or if its just a fall thing? I was thinking about getting lemon, cherry, and then another fun flavor...I tried a green tea splenda flavor yesterday that was so good! Of course it will depend on whats available that day because I really just plan on having someone go down there the day of the wedding and buying a few gallons.
I don't know...the theme is kind of rustic/modern/vintage. Limes are a big theme, as are some literary elements and deep plum.
I don't love the idea of self-serve. Whenever I scoop icecream or sorbet my hands get all sticky.
But since your other hors d'oeuvres are stationery, I think you can get away with it. But if you can afford it, I think having it served would be better.
@sboston06: I'll check and see how much it is for them to serve it. Thanks for your input!!
The cups are definitely "modern vintage" so I would guess they'd look okay with your decor. :)
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I don't know about you guys but I LOVE Rita's Italian Ice!! They just came out with a new flavor, cranberry, and I am HOOKED!!! I'm thinking about serving it at my wedding. I am kind of thinking I will either
a.) have it out for them to enjoy during the ceremony
b.) have it out during cocktail hour since the only other apps will be cheese, crackers, and fruit.
c.) have it after dinner. We are also having cupcakes for dinner...no cake.
Also, I'm unsure about how to display it? I was thinking maybe getting good quality, clear plastic cups to serve it in? Maybe putting the tubs of it in a nice big galvanized tub with ice and people serve themselves? I'm using a lot of mason jars in my centerpieces, but I think they would be too large and not shallow enough for people to eat out of.