6
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Actually I wanted to see that movie again but don't remember the name. Story goes like this, if anyone could recall.

A girl had two options of guys, one of which is struggling writer and one is rich successful ad agency owner. She lives with her brother and discusses her two simultaneous relationship with him. Brother is reimbursed for a chewing gum ad.

In the end after dating two guys at same time she decides that she will marry rich guy. But as usual writer guy runs for the girl and girl realises her love for him and miss her flight intentionally. At end both meet.

Probably shot in Washington DC or maybe Texas. Movie is around 2003-2009. Probable IMDb rating could be 5-6. I have seen it at friends place, 3 years ago.

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    Please try to give as much detail as possible: Where you watched the movie or TV show | When you watched the movie or TV show | Any idea of how old it was | Any idea of country of origin (if known) | Whether it was animated or not | Any distinctive detail
    – BCdotWEB
    Oct 28, 2015 at 9:55

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4
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You're looking for My Girlfriend's Boyfriend from 2010 with Alyssa Milano.

Jesse, in a moment of bold self-confidence, introduces herself to Ethan, a struggling writer. And then in walks [rich ad executive] Troy, and in a moment of bold self-confidence, he introduces himself to Jesse. Jesse falls in love with both men, who happen to have a lot in common but still seem very different. What will happen when Jesse has to tell the truth?

Everything you mentioned is there (her brother's gum ad, choosing the writer and missing the flight), but there's a twist:

The rich guy never existed. The writer made him up.

I posted this answer before, but the questions are different. Here's the trailer:

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