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This sort of serenade and presentation of a rose is a great opportunity for your guys to get more comfortable making public gestures towards women. I'd really work on getting the guys to play along here. It's not a marriage proposal after all! And even if they flub it, the girls will be moving on to the next house and it will be over in a minute. Move the girls to the back of the crowd for this one (ask them to consider it giving the guys a good life lesson) and let the guys move outside their comfort zone for just a minute.
Regarding the 3-way socials, I think that's a great idea if you can get anyone to play along. Attending both the sorority and fraternity philanthropy events is a great way to start, and depending on your campus and the kinds of events, can be the "not to be missed" on campus kind of events. Have as many members show up as possible, dressed for success, in letters, and ready to jump in and play along.
Also, there's a term in business called an elevator pitch. It's a sales pitch that can be shared in total in the time it takes to ride an elevator. Every one of your members, including the most shy, should be able to explain your organization in 30 seconds. It takes a lot of practice to get right, but it has multiple levels of benefits, not the least of which is getting more comfortable talking with strangers.
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"Traveling - It leaves you speechless, then turns you into a storyteller. ~ Ibn Battuta
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