‘Everybody Loves Raymond’: How Many Times Did Robert and Amy Break up?

Everybody Loves Raymond may have been all about Ray Barone and his wife, Debra Barone, but other fan-favorite characters emerged during the show’s nine-season run. Robert Barone, Ray’s older brother, was beloved by fans. As the series progressed, viewers rooted for him to find his love and settle down, noting that Amy MacDougall was his perfect match. Eventually, just that happens, but do you have any idea how many times the couple broke up before they finally got married? It’s a lot.

Amy MacDougall started dating Robert Barone in season 1 of Everybody Loves Raymond

When fans first met Robert, he was characterized as pathetic and needy. While it’s never mentioned, it’s implied that he hadn’t dated regularly since his divorce. To lift his spirits, Debra introduced him to her friend, someone she had worked with previously. Amy MacDougall was introduced for the very first time in the show’s very first season.

The cast of 'Everybody Loves Raymond'
The cast of ‘Everybody Loves Raymond’ | Monty Brinton/CBS Photo Archive/Getty Images

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Her first appearance on the show, in the season 1 episode, “Who’s Handsome?” marks the beginning of the pair’s relationship. While she isn’t seen in every episode, it’s implied that Amy and Robert’s relationship began to heat up almost immediately. The pair eventually got married, but the road there wasn’t exactly smooth.

Amy and Robert broke up several times before they made it to the altar

When fans first met the Barone family, Ray and Debra were settled into married life. While the pair bickered, their marriage was largely on solid ground. The same was true for Marie and Frank Barone, who, after decades together, settled into their own toxic dynamic. Robert and Amy were different. The pair provided viewers with the relationship drama that is often needed to sustain a sitcom.

According to IMDb, before they walked down the aisle, Robert and Amy called it quits four separate times. Robert and Amy broke up for the first time in season 3, after nearly two years together. They reconnected several months later and finally consummated their relationship.

Madlyin Sweeten, Monica Horan, Sawyer Sweeten, Brad Garrett, Doris Roberts, Ray Romano, Patricial Heaton, Peter Boyle and Sullivan Sweeten
Madylin Sweeten, Monica Horan, Sawyer Sweeten, Brad Garrett, Doris Roberts, Ray Romano, Patricia Heaton, Peter Boyle, and Sullivan Sweeten | Richard Cartwright/CBS Photo Archive/Getty Images

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Their second attempt at a relationship didn’t last nearly as long as their first. Annoyed that Robert gave her pearls instead of an engagement ring, Amy called off their relationship in season 4. They reconnect again after Robert was injured at work but broke up after he revealed his infidelity. They briefly reconnect in season 6, but things didn’t last. Robert finally proposed in season 7. Amy and Robert’s wedding day strongly mimicked their early relationship, but eventually, they became man and wife. Writers featured the marriage during the show’s final seasons.