Many times in his life, hockey legend Wayne Gretzky has gone on TV and asked Oprah Winfrey for her hand in marriage. Here are five of the most iconic times Wayne Gretzky asked Oprah to be his wife on live television, ranked by how awkwardly he responded when she turned him down.
5. The time Wayne Gretzky paid Oprah’s studio audience to wear shirts that spelled out, “Marry me Oprah”
In July of 1999, Wayne Gretzky attempted to propose to Oprah on her show by paying members of her studio audience to wear shirts that spelled out, “MARRY ME OPRAH,” and all stand up when he walked onstage during the live broadcast. Unfortunately, the plan backfired pretty spectacularly. Oprah thought the proposal was a joke and laughed it off, so Gretzky had to convince her that he was serious, which took him a while. After Oprah finally realized that Gretzky sincerely wanted to marry her, she delivered a decisive no, and Gretzky awkwardly tried to transition the conversation to hockey by shakily asking, “So have you been watching much hockey lately? I have been watching lots of hockey,” while looking down at the ground, unable to make eye contact with anyone. It was a little awkward, but compared to some of Gretzky’s other disastrous proposals, it was nothing.
One time, when Oprah was a guest on Late Night With David Letterman, Dave smiled at Oprah and said, “There’s someone here who’d like to ask you something.” The band started playing “Here Comes The Bride” (which Gretzky had asked them to play beforehand), and Wayne appeared from backstage carrying the Stanley Cup, which was filled with roses. He then got down on one knee in front of a visibly shocked Oprah and said, “Mrs. Winfrey, you’re the love of my life. You’re my sun, my stars, and my moon. Oprah, will you be my loving wife?” and handed her the rose-filled Stanley Cup. Oprah shook her head and Wayne stood up, not knowing what to do. Oprah tried to hand him back the Stanley Cup, but Wayne was frozen, his face red with embarrassment. After a few minutes of painful silence, Oprah just carefully set the cup down on the floor and returned to finish her interview with Letterman. Dejected, Gretzky bent over to pick it up, accidentally knocked it over with a loud clang, spilled some of the roses, and walked offstage. All in all, it was pretty damn awkward.
3. The time Oprah and Wayne Gretzky were hosting a telethon together and Gretzky immediately proposed and then kept trying to play it off as a joke for two hours after she said no
The Hurricane Harvey Relief Telethon turned into an awkwardness endurance test for viewers about 15 seconds in, when Wayne matter-of-factly asked Oprah if she would marry him and she quickly responded no without batting an eye before looking into the camera and launching into a request for donations. For the remainder of the telethon’s grueling, uninterrupted 120 minutes, Gretzky continued to try to explain away his proposal as a joke, saying, “I was only kidding with the proposal thing. I mean, I’m a happily married man,” while Julia Roberts fake-laughed and Oprah mostly ignored him. Only number three, you ask? Yep, Gretzky’s televised proposals to Oprah get even more awkward.
In this elaborate proposal attempt, Gretzky actually hired an ordained minister to interrupt an episode of her show and ask her to look under her chair, where Gretzky was crouched in a tuxedo clutching an engagement ring. Gretzky proposed, and Oprah said no. Wayne then froze up completely and refused to move. After 15 minutes of coaxing from Oprah, the priest, and the studio audience, Oprah finally decided to just give up on getting Wayne to come out from under the chair and continued with the remainder of her show, with David Blaine doing magic tricks while Gretzky silently wept, crouched beneath Oprah’s chair in his tuxedo. It was Awkward with a capital A.
1. The time Oprah rejected Gretzky’s proposal, so he immediately called his wife to beg if she’d have him back and she said no so he asked Oprah again
Oprah was serving as a celebrity guest on Dancing With The Stars while Gretzky was a contestant, and it led to his number-one most awkward response to getting turned down. In the middle of his dance routine, Gretzky stopped, looked Oprah in the eyes, and said, “This is for you,” before abandoning his partner to perform a beautiful solo dance that ended with him on his knees, engagement ring in hand, asking for Oprah’s hand in marriage. Oprah said, “The dance was spectacular, Wayne, but no.” Wayne immediately began to panic, shouting, “Shit, shit. What have I done?” He took his phone out to call his wife and ask if she’d have him back, since he had apparently dumped her earlier that day in preparation for his proposal to Oprah. After his wife refused to re-marry him, Gretzky regained his composure and immediately repeated his entire engagement dance for Oprah before asking her again to marry him. Oprah responded by getting up and leaving. It was brutally awkward from start to finish, and that’s how it earned its place at number one on this list.