Christmas in Boston (2005) on Netflix

Now in young adulthood, Gina and Seth have been pen pals for thirteen years. They have graduated from handwritten letters when they started corresponding to email, but with both being insecure with who they are as people have decided not to exchange telephone numbers. Even when they have discussed exchanging photographs of the other, they have sent photos of their more outgoing best friends, Ellen and Matt, passing them off as themselves without telling either Ellen or Matt. Each has been there for the other through every major event that has happened in their lives, and as such, they have both fallen for the other without either admitting it to themselves or having the nerve to tell the other. Living in different cities - Boston and Denver - they have never even seriously considered meeting in person, until now. Seth, a junior executive at a toy company, is heading to Boston just before Christmas to attend a toy convention, which Gina, a struggling reporter stuck in "obituary" purgatory at her newspaper, is given her first real reporting assignment to cover. Gina knows that Seth is on the attendee list, tells him that she knows he's coming, but she doesn't tell him that the convention is her assignment. They both know that they have to meet at least once, and as such convince their "photo" alter egos, Ellen and Matt, to take their place at that meeting. The first problem is is that Ellen and Matt, after acting more like themselves than what Gina and Seth are supposed to be, begin to fall for each other, which causes issues in their friendships with Gina and Seth. The second problem is that Gina and Seth meet at the conference without knowing who the other is, and they slowly fall for each other, not wanting to betray their feelings for who they believe are Seth and Gina in Matt and Ellen. But a further issue arises when Seth knows that "the reporter" he is falling for has some sensitive information gleaned accidentally from him that could ruin his career if it came to public light, but that could break open her stagnating reporting career.