Jonathan Trager

Living… in New York with his fiancé, Halley. Jonathan spends a lot of time living in his imagination and memory – he often thinks back to a day years ago in which he met a wonderful woman at Bloomingdales. After one of the most magical nights of his life, he and the Englishwoman, Sara, lost touch, though he certainly hasn’t forgotten her.

Profession… producer for ESPN. Jonathan gave up his childhood dream of being a documentary filmmaker in order to make a decent living. A man who is engaged must have a lucrative job, at least the way he figures.

Interests… his best friend Dean. Jonathan and Dean have been inseparable since college, where they first met. They’ve always been able to rely on each other for advice, support and a good laugh.

Relationship Status… engaged to Halley Buchanan, though he’s beginning to have a few doubts. Jon can’t seem to get Sara, a woman he only met once, out of his head. “It’s like Halley is The Godfather Part II,” he explains to John. “That was an incredible movie, might be better than the original. But no matter how much you love The Godfather Part II, you still have to see the original to understand and appreciate the sequel, don’t ya?”

Challenge… finding the woman he was meant to be with. Jonathan knows in his heart that Halley is not the one for him. It’s no coincidence that he keeps harking back to his one night with Sara. And Sara, as it happens, does the same. The fact that they didn't exchange any contact information the night they met, preferring to leave it to chance, is now looking like a big mistake. New York is a big city, and it's hard for any two individual people to find each other – or find each other again, in this case.

Personality… soft-spoken, affable and hopeful. In the words of his friend Dean, Jonathan “never looked the part of a hopeless romantic.” At heart, though, Jon is a fighter willing to risk everything for a shot at true love.