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Several things to think about:
1. Many will be afraid of exposing personal information in a program that might contain spyware/adware that they're not aware of.
2. Why do it Windows-based? The whole world is shifting to software on demand anyway. Don't forget that many will want to access it from a friend's house, vacation, etc.
3. It's a nice gimmick, but again, what will set you apart from existing dating sites (don't get me wrong, I think existing sites SUCK and there's a lot of room for new players, but still.. Windows-based?)
4. This would have worked great 4 years ago. Nowadays many people have pics stored in all kinds of image hosts, blogs, etc.
5. Privacy advocates will say customers are exposed to more risks as opposed to a true web-based application (IP shit). Thing is, it will have many teenagers using it, so parents will probably agree with them.
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