Ed prepares to travel from San Diego to the Philippines to meet his 23-year-old girlfriend Rosemarie for the first time. His family and friends are concerned that she's taking advantage of his generosity.

Ed packs gifts to take to Rosemarie and her family, but he worries that she won't feel a connection. When he arrives in the Philippines, she's surprised by his appearance, and Ed makes a startling request.

Ed presses Rosemarie for information about her ex-boyfriends. He makes a request that upsets her, and they work on building trust. Then Rosemarie takes Ed to her hometown to meet her family.

Ed spends an eye-opening night at Rosemarie’s home, with her father sleeping in the same room. Then they go on a romantic island getaway, and Ed reveals that he's not interested in having more children.

Ed reveals a secret, and Rosemarie feels betrayed. He's overwhelmed by emotion when he returns to San Diego, and he catches up with his daughter, Tiffany.

After ending his rocky relationship with Rose, Ed is making moves to get back in the dating game. He joins some dating websites, but he also has his eye on a friend who works at his favorite local restaurant.

Ed's mom helps him prepare for his second date with Liz. Since she is nearly 30 years younger, Ed needs to overcome her skepticism about their age difference in order to convince her they can be more than just friends.

Ed takes Liz on a road trip to a friend's wedding in the mountains. On the way, Ed gets a phone call from the hotel that they can no longer provide a room with two separate beds -- he and Liz will have to share.

When Liz finally agrees to be Ed's girlfriend, he ruins the moment by immediately asking her to meet his daughter, Tiffany. If Tiffany is unconvinced that Liz is right for her father, it may derail the relationship entirely.

After his rough breakup with Liz, Ed transforms his appearance and heads out on a date. Although he's sporting a new look, he's still struggling with the past. Later, a date gets awkward after Ed cries at dinner.

Ed travels to Mexico to take a chance on a relationship with a friend of a friend, but a frightening incident cuts their first date short. Later, Ed wants to take his relationship with Kaory to the next level, but he may once again be moving too fast.

Ed attempts to impress Kaory's family. Later, he gets an unexpected response when he asks Kaory how she feels about him. After returning to the US, Ed struggles when he loses an old friend, but a surprising reconnection helps him through.