First comes love, then comes marriage, or so goes the old rhyme. When people think they have met the one, it is only a matter of time until they pop the question.
Hopefully, after that, it is all smooth sailing. Sometimes, not so much. Sometimes the proposal is rejected, or the couple gets torn apart. For whatever reason, a wedding doesn’t happen.
With the turmoil that writers often put couples through, it would be easy to give up. However, some refuse to.
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Some say, “So what if we didn’t end up getting married the first time around? So what if I got rejected, or I lost you? You’re with me now, and I love you, so I’m going to propose to you again, and again, until I get a yes, and a wedding, and get to call you my wife/husband!”
It takes a lot to propose twice, but these paramours did it. Some of them proposed more than twice, and you might be surprised by who I’m talking about.
Here’s a list of the those so determined to tie the knot that they proposed not once, but twice (and sometimes thrice).
Killain Proposes To Emma — Once Upon A Time
On Once Upon A Time Season 6 Episode 13, Emma found a ring among Killian’s things and forces a proposal, which would be all well and good if he weren’t hiding the fact that he killed her grandfather. This leads to an engagement, the truth coming out, a fight, and Killian being whisked away by a villain. On Once Upon A Time Season 6 Episode 17, after overcoming those determined to keep them apart, Killian once again gets down on one knee and pledges to always be by Emma’s side. She said yes the first time, and then fought like hell to get him back, so it’s no surprise when Emma, once again, agrees to be Killian’s wife mere episodes after the first proposal.
Barry Proposes To Iris — The Flash
The Flash Season 3 Episode 14 ends with Barry Allen asking Iris West to marry him. Since we didn’t actually see her say yes, fans had a feeling that this wasn’t the “real proposal” WestAllen fans had been waiting for. Sure enough, when Iris learns that Barry only proposed as a way to change the timeline so she wouldn’t die, she begins to have doubts. The two come apart briefly, but on The Flash Season 3 Episode 17 they come back together, and WestAllen fans get the magical proposal scene they were waiting for. What’s better than Grant Gustin singing “Running Home To You” as he gets down on bended knee? Not much. This scene makes a relatively corny musical episode and two proposals in less than five episodes completely worth it.
Daniel Proposes To Emily — Revenge
The first time Daniel Grayson proposed to Emily Thorne on Revenge Season 1 Episode 13, it was magical. It was aboard the yacht where they first met. He was wearing “the jacket.” Daniel refused to be deterred by the rain, pouring his heart out to the woman who he thought was the love of his life, and she accepted. Then Daniel’s true Grayson colors showed. Emily became disgusted with him and took the first excuse to end things when she thought her revenge was over, only renewing the relationship when it was necessary. His second attempt on Revenge Season 2 Episode 19 put Emily on the spot about their future on live television. Afterward, he issued an ultimatum: get engaged or break-up. Emily said yes for ulterior revenge motives, but what we have here is an example of a guy who should probably have only proposed once.
Robin Proposes To Marian — BBC’s Robin Hood
This one is a bit of a cheat because we never saw the first proposal. When the series begins, Robin is returning from The Crusades. Over the course of the season, we learn that he and Marian had been engaged before he left her to fight in the war, effectively ending the relationship. She is none too happy to see him upon his return, but throughout season one, the two reconnect and eventually reconcile. On BBC’s Robin Hood Season 2 Episode 9, Marian’s father gets killed. After the two have buried him, Marian asks Robin if he wants to say a few words, and the words he chooses are a proposal. It shows how far the two have come that Marian accepts, even if she takes her time about it. Really, these two deserved better than how they ended. I’m still not over it.
Lavon Proposes To Lemon — Hart of Dixie
Lavon Hayes’s proposal to Lemon Breeland on Hart of Dixie Season 4 Episode 9 was the perfect proposal. Taking your girlfriend to the most romantic spot on your property where lit candles are spelling out “Will You Marry Me?” What could be better? Except that the proposal was meant for someone else. Lemon and Lavon happening upon it when he was talking about their future together was a mere coincidence. Lavon was thrilled to be engaged to the girl of his dreams, even if it happened by accident. When he fessed up at their engagement party, Lemon was hurt and furious. So Lavon set up a romantic proposal to make it up to her, but their friends needed them. The ended up in a car together, which Lavon pulled over, proposing to Lemon on the side of the road. This time it was real, and Lemon was touched.
Max Proposes To Lorelai — Gilmore Girls
The first time Max proposes to Lorelai on Gilmore Girls Season 1 Episode 21, she does not take him seriously. They were fighting, and as Lorelai says, “a proposal has to be more than a desperate attempt to end a bickering match.” She continues, saying, “It should be magical. There should be 1000 yellow daisies.” She convinces Max that proposes then is crazy, and it seems like that will be the end of it. Later, Lorelai shows up to work to find 1000 yellow daisies for which the delivery man says she has to sign. Over the phone, Max tells her that she was right in saying his first proposal was not the done right, but she was wrong in saying he only did it because they were fighting. No matter what team you’re on, you have to admit, Max knew how to propose. Sure, the first time went over really bad, but the second time he really got it right.
Clark Proposes To Lois/Lois Proposes To Clark — Lois and Clark: The New Adventures of Superman
Since Clark spent the beginning of Lois and Clark: The New Adventures of Superman Season 2 Episode 22 trying to tell Lois that he was Superman, when he pulled her aside at the end of the episode, fans were expecting him to come clean. Instead, he proposed. Maybe he should have told her first since her response was the famous “Who’s asking? Clark, or Superman?” They struggled to figure out their new dynamic once Lois knew who Clark was and that he had been lying to her for two years. Clark came close to proposing again once things calm down, but Lois beat him to it on Lois and Clark: The New Adventures of Superman Season 3 Episode 7. It took them two proposals, not to mention three weddings to get married, but that’s a different story. For now, let’s just say that when it comes to their love, these two don’t give up.
Kevin Proposes to Robin — How I Met Your Mother
On How I Met Your Mother Season 7 Episode 16, Robin’s boyfriend Kevin asks her to marry him. She tells her friends she wants to say yes, but first, she needs to tell Kevin that she can’t ever give him children. Once she has explained everything to him, Kevin once again asks “Will you marry me?” He says that they could always adopt, and Robin clarifies that she also has no desire to become a mother and she doubts that will change. Once again Kevin asks “Will you marry me?” Robin presses the point. She does not want Kevin to grow to resent her. Eventually, and by eventually, I mean later that episode, they realize that Robin not only being infertile but not wanting kids is too insurmountable for them. For a while though, it seems like Kevin would be willing to sacrifice anything to make Robin his wife.
Chandler Proposes To Monica — Friends
All Friends fans remember Chandler Bing’s romantic proposal to Monica Geller on Friends Season 6 Episode 25, but only die-hard fans will remember that this was, in fact, the third time Chandler proposed to Monica. The first time was on Friends Season 5 Episode 15 when after upsetting Monica, Chandler asked her to marry him because he was sorry. Monica said being sorry was not a good reason to get married, but she did forgive him for his missteps. On Friends Season 5 Episode 24. Monica was on a winning streak while gambling in Vegas. Chandler said that if she rolled a hard eight, they should get married. They almost eloped until seeing a drunk Ross and Rachel leaving the chapel snapped them back to their senses. Thankfully those proposals didn’t take, because the actual proposal was tear-inducing perfection.
Cole Proposes To Phoebe — Charmed
Most girls don’t dream of being proposed to in a dumpster covered with demon goo, but that’s exactly how Cole proposes to Phoebe on Charmed Season 4 Episode 8. He blurts out “Marry Me?” while the two are recovering from a demon altercation catching Phoebe completely off guard. Phoebe’s loves Cole, but she is a free spirit struggling with grieving for Prue and her new role as a big sister. Phoebe is unable to give Cole the answer he wants, or any answer for the next couple of episodes. Then on Charmed Season 4 Episode 10, the two are possessed by old lovers who want to get hitched. This leads to a chapel, a wedding dress, and Cole getting shot. Once everything is back to relatively normal, Phoebe asks Cole to ask her the question again, and this time, she gives him the answer he has been waiting for.
Leonard Proposes To Penny — The Big Bang Theory
On The Big Bang Theory Season 5 Episode 23, Leonard freaks Penny out in a major way when he blurts out “Will You Marry Me?” right in the middle of sex. He almost proposes again on The Big Bang Theory Season 6 Episode 16, but Penny stops him, and they agree that she should propose next, which she does on The Big Bang Theory Season 7 Episode 12 after a career failure and a lot of alcohol. Leonard rejects her because he knows she is proposing for the wrong reasons. On The Big Bang Theory Season 7 Episode 22, Leonard tells Penny he regrets not accepting her proposal. Since Leonard proposes more often, Penny agrees to even the score, Penny proposing again. She has to do it twice because Leonard messes with her. On The Big Bang Theory Season 7 Episode 23 the two finally mutually agree to get married. Wow! That’s a lot.
Jesse Proposes To Becky — Full House
The first time Jesse proposes to Becky on Full House Season 2 Episode 21 the two nearly elope in Vegas. The proposal was impulsive, a result of jealousy and misunderstandings that culminated in the couple declaring their love for the first time. Once Becky calmed down from the high of being in love and proposed to, she realized that she and Jesse are not ready to tie the knot. She leaves Jesse at the altar, devastating him. Somehow though, the couple comes back together and pulls through. Over a year later on Full House Season 4 Episode 1, Jesse learns he is actually married to a girl from his past. After ending his marriage, he asks Becky to be his new wife, and she agrees.
Aaron Proposes To Sabrina — Sabrina the Teenage Witch
The first time Aaron proposes, on Sabrina the Teenage Witch Season 7 Episode 17, Sabrina thinks he is only doing so because mischievous magical beings are making him. She rejects him in what is a humiliating display, and he leaves with his tail between his legs to catch a flight to another city. When Sabrina realizes that Aaron was proposing of his own free will, she goes after him. He proposes to her again at the airport with gum on his pant leg, and Sabrina says yes setting up for the rest of the series. Of course, we all ship Harvey and Sabrina, but it takes a big man to propose again after such a humiliating rejection. Hopefully the next time he proposed it was to his soulmate.
Cyrus Proposes To Alice — Once Upon A Time In Wonderland
On Once Upon A Time In Wonderland Season 1 Episode 1 Cyrus proposes to his girlfriend Alice on a cliff overlooking a lava pit. Once sees saw what he is about, she burst out with a yes before he can even finish. They kiss, and it is all kinds of romantic. Then the Red Queen of Wonderland shows up and pushes Cyrus off the cliff and into the Lava pit, presumably killing him and devastating his fiance. When Alice discovers that Cyrus is not dead, she goes on a quest to find him, taking up the first half of the season/series. The lovers are finally reunited midway through the season/series, and while their reunion is not without its fair share of perils, they find a moment alone on Once Upon a Time in Wonderland Season 1 Episode 9 for Cyrus to once again ask for Alice’s hand. This time he even has a ring.
Casey Proposes To Dawson — Chicago Fire
When Matthew Casey proposes to Gabriela Dawson on Chicago Fire Season 2 Episode 22, she does not have a chance to answer before they are both called about a fire. The repercussions of that fire are so great that the subject cannot be revisited right away. However, on Chicago Fire Season 3 Episode 2 Casey surprises Dawson with a romantic rooftop proposal. Thankfully Dawson’s answer is, and would always have been, yes.
Lucas Proposes To Peyton — One Tree Hill
On One Tree Hill Season 5 Episode 5, it is revealed that Lucas proposed to Peyton during the time jump between seasons four and five, but she turned him down. She said she wanted to marry him someday, but Lucas, heartbroken and unable to wait, effectively ended the relationship. After an almost wedding to someone else and a lot of drama, Lucas calls up a girl and asks her to elope with him on One Tree Hill Season 5 Episode 18. One Tree Hill Season 6 Episode 1 reveals that girl to be Peyton. While they do not end up eloping in Vegas as planned, they are, from that point, officially engaged. Then on One Tree Hill Season 6 Episode, 15 Lucas proposes again. Yes, they are technically already engaged, but now he has a ring, so he brings her to “their spot” and gets down on one knee, reminding Peyton that he always knew her.
Oliver Proposes To Felicity — Arrow
Then Mayoral candidate Oliver Queen makes a public declaration of his love for Felicity Smoak when he proposes to her On Arrow Season 4 Episode 9. She says yes, and things seem perfect. Then Felicity is paralyzed, and she finds out about Oliver’s secret illegitimate son. It proves too much for the couple to overcome and Felicity leaves him. The two sort out their differences toward the end of season five and become a couple once more early on in season six. On Supergirl Season 3 Episode 8 when the CW did its big DC crossover for the year, Oliver is inspired at Barry and Iris’s rehearsal dinner and proposes to Felicity again. Felicity says no, a little gunshy after the last time the tried it, but she gets over it and ends up proposing to him on Legends of Tomorrow Season 3 Episode 8, leading to an impromptu double wedding.
Lorelai Proposes To Luke — Gilmore Girls/Gilmore Girls: A Year In The Life
On Gilmore Girls Season 5 Episode 22 Lorelai Gilmore reminds us why she is a feminist icon by proposing to Luke Danes. He answers in the affirmative in the premiere of season six, but when he drags his feet a bit too much, the two end up splitting. They do eventually reconcile on Gilmore Girls Season 7 Episode 22, which is the series finale. That would have been it, except after a decade off the air, Gilmore fans were gifted with a four-part Netflix series. On Gilmore Girls: A Year In The Life Season 1 Episode 4 Lorelai once again asks Luke to make an honest woman out of her. While fans wish they had been married for the past ten years, it was a great scene. Also, thankfully, this time they go through with it.
Mike Proposes To Phoebe — Friends
On Friends Season 9 Episode 16, Mike and Phoebe break up because Mike never wants to get married. However, on Friends Season 9 Episode 23, Mike finds out that Phoebe’s new (old) boyfriend David is proposing to Phoebe and that Phoebe plans to say yes. He flies to Barbados to propose to Phoebe. She turns him down saying she never needed a proposal from him, she just needed to know that it would happen someday. Turns out, someday is next year. On Friends Season 10 Episode 5 Phoebe keeps screwing up Mike’s proposals by accident. She tries to fix it by proposing to him, only to have people say he has no balls. In the end, it doesn’t matter. The two get engaged at a restaurant where Mike proudly announces that Phoebe is going to be Mrs. No Balls.
