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What's your rationale behind your proposal to force users to do stuff? Is it to make initial conversation easier? Well, could be an icebreaker, that's true. Do you think it comes across as sincere intermediation or as some kind of forced thing both parties will rebel against?

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think about a cocktail party. the host comes in, introduces everybody around. you meet new people, talk about stuff. generally a good host will tell you a little about the other people you haven't met, and say something like 'they'd be a good person to talk to about X', where x is some topic you know you have in common. most dating sites don't do this -- there are no introductions, no incentive to converse. you get to know/be comfortable/uncomfortable with people through interaction. a guided interaction is exactly what most online dating applications are missing.

It's a way to find out what kind of person your 'opponent' is and to get to know them, as well as to have fun, thus creating an emotional bond with them - a reason to 'see' them again. A short, goofy game, akin to a Mario Party or Wario Ware video game, would be perfect for this, I think.

Check out http://images.google.com/imagelabeler/

The creator (or so) once told in an interview that people feel connected when playing this game successfully together.

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