Meeting your ex's new fling? Ever been a third wheel on your crush's date? Show us your most awkward situation and what you might wear or do to get out of it!
Style a look from emerging designer and FIT graduate Sergio Guadarrama for your chance to win a trip to the Polyvore Live fashion show during NY Fashion Week.
Style a look from emerging designer and FIT graduate Lauren Bagliore for your chance to win a trip to the Polyvore Live fashion show during NY Fashion Week.