Rob Lowe Asked Melissa Gilbert to Marry Him When She Was in Love With and Dating Someone Else

Just as Melissa Gilbert was finally moving on from Rob Lowe, he asked her to marry him. After his whirlwind romance with Princess Stephanie of Monaco ended, he suddenly came to the decision that he wasn’t going to “live without” Gilbert. The only problem was, the Little House on the Prairie actor was with someone else.

Rob Lowe and Melissa Gilbert
Rob Lowe and Melissa Gilbert | The LIFE Picture Collection via Getty Images

Melissa Gilbert and Alan Greenspan

Gilbert met Alan Greenspan, an agent, at a party. Together, they made an early exit to escape to the Hard Rock where they could get to know each other better. Soon after that, a relationship formed.

“We saw each other again the following weekend when he invited me to watch him play in the Hollywood Softball League at Balboa Park,” Gilbert wrote in her memoir, Prairie Tale. “Then he came back to my house for lunch and a relationship blossomed. It happened that easily.”

Gilbert felt she “lucked out” with Greenspan.

“I would pinch myself whenever I thought about Alan,” she wrote. “Not only was he breathtakingly handsome, he was also a kind, warm, generous, funny, easygoing guy.”

Rob Lowe asked Melissa Gilbert to marry him

While Gilbert was falling in love with Greenspan, Lowe was involved with Princess Stephanie of Monaco. But just as quickly as the love affair began, it ended. When it was over, Lowe called up Gilbert.

“I knew what he wanted, what he was going to say, and I didn’t want to have that discussion,” she wrote. “But he pleaded with me to change my mind and eventually broke me down.”

Rob Lowe and Melissa Gilbert
Rob Lowe and Melissa Gilbert | The LIFE Picture Collection via Getty Images

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Gilbert spent hours “preparing my responses to all the apologies and entreaties I knew he was going to make.” But Lowe didn’t want to just get back together.

He admitted to breaking her heart “far too many times,” and told her he wasn’t going to “live without” her. He told her “this time is different.”

When Gilbert asked Lowe what the difference was, he got down on one knee and said: “Because this time I want you to marry me. I am formally asking for your hand in marriage. Will you marry me?”

Melissa broke up with Alan to be with Rob

Gilbert told Lowe she needed time to think.

“I really didn’t know what the hell to do,” she wrote. “In the meantime, I had a special man in my life who was calling me throughout this quandary and asking me to dinner and movies, asking me to hang out with him as we had been doing, and asking me if he could bring me soup or just sit with me when I told him that I’d been lying low because I wasn’t feeling well.”

Every time Gilbert thought about saying yes to Lowe, she heard a voice in her head that said, “Don’t do it. You already have a wonderful guy. He’s sweet. He’s caring. He adores you. You’re going to break his heart and then you’re going to be sorry.”

Nevertheless, the Little House actor made a pros and cons list that pointed in the direction of Lowe. She ended things with Greenspan and accepted the Oxford Blues actor’s proposal.

Gilbert and Lowe never did make it down the aisle, though. They broke up about a year later.