Movie where woman makes bet with her boss about homeless man

So a few years ago, I remember watching this movie about a corporate woman who made a bet with her boss or one of her coworkers about transforming a homeless man (possibly a conman? I think he was selling knock-off watches or some kind of fake merchandise outside her office building) into a respectable business man. The movie takes place in some kind of big city, probably New York and I’m pretty sure the movie was a TV movie, possibly a LifeTime movie? Anyway, so the woman succeeds and makes society fall in love with this new mystery mogul and he’s appearing at different events and charity functions etc. And the woman and this transformed homeless man end up falling in love during this transformation, but then he finds out about the bet she had made and loses all trust he had in her so she has to prove to him that her feelings were genuine and not part of the bet.

I’ve been trying to find this movie for the longest and it’s bothering me so much that I can’t remember what it’s called so if anyone could help me figure it out, I’d be so grateful!!

4 thoughts on “Movie where woman makes bet with her boss about homeless man

  1. Sounds a lot like trading places, with Eddie Murphy and Dan Aykroyd, definitely not a life time movie though

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