Worst Holiday Proposal Situations

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Maybe I watch too many rom coms, but if you’re a girl like me, at one point or another you’ve daydreamed about opening a huge gift from your BF during the holidays—only to find a tiny box inside containing the most beautiful engagement ring! While it’s cheesy and cliché, getting proposed to on Christmas (or Hanukkah or Kwanzaa) can be very romantic—if done the right way.

Yet, we all know things rarely go as planned, leaving plenty of room for this would-be-romantic sitch to go horribly wrong! Here are some of the worst holiday proposals I hope you (or I for that matter!) never have to deal with.

-Samantha Sutton

Mid-Family Gathering

Picture this: You’re sitting at the dinner table, trying to follow Aunt Debbie’s rant about how your generation is addicted to technology, when your boyfriend has an announcement to make. Surprise! You’re getting engaged—and now your mom is nearly choking on her chicken. Yikes!

I don’t know about you, but this situation sounds less than ideal to me. Between the pressure to say yes (or no, depending on how your fam feels about this dude) and the embarrassment you may feel now that you’re the center of attention (oh hey, remember that baby in a manger, anyone?), you may be wishing you were anywhere but in this sitch—no matter what your answer is. If you feel your man may pull this, mention to him well beforehand how much you would love to be proposed to privately…without grandma staring at you while you awkwardly answer the question.

18 Comments

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  • Christina:

    Not into cliches

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  • avatar
    sarentia:

    Santa suit? Why?! That just sounds awful. Don’t know how anyone could think that’s a good idea.

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  • lilyrose55:

    I know people that have been proposed to at the holidays and that’s great for them, but I do not want any guy to propose to me on any holiday for one simple fact… what if the relationship ever goes bad?? I don’t want to have a holiday ruined because I’ll always think of it as the day _____ proposed to me.

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  • jasminesmommy:

    I never got a proper engagement either so I can’t relate!

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  • bobbysgirl777:

    I never even got a real proposal. It was always just one day we’ll get married, and then we just set a date. I would have loved an thought out proposal, because it is the though that counts.

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    1. bobbysgirl777:

      *any

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  • avatar
    danghsia:

    i don;t mind the santa suit though

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  • avatar
    danghsia:

    #2 is really bad

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  • megiam:

    I’m most definitely #3. I’ve been with my boyfriend for 5 years, well 5 years in just another month. I don’t know how he will propose and I know its on his mind, but it will not be in a santa suit or in front of his family. Actually, he’s really stressed about it because he thinks I deserve some over the top proposal…and I don’t. Makes me feel bad that he is under so much pressure (and not from me, everyone we know gives the “when ya getting married” talk).

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  • Joy:

    #5 – agree no santa suit!

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  • Joy:

    #4 – funny – not too bad though – it never really gets that cold here in california – I still think it’s cute but I can understand if I lived in Chicago or something – I might not like it.

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  • Joy:

    #3 – that’s not so bad – give the guys a break – they are trying to make it special – so I think it’s kinda cute that they try to be romantic of what a girl wants

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  • Joy:

    #2 – yep totally agree I don’t want a drunk proposal

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  • Joy:

    #1 -yea no I don’t want him to propose in front of the family. I want it to be just me and him.

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  • Crispy:

    hahaha typical

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  • penelope:

    too funny haha

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  • avatar
    sunnytam:

    Holiday proposals are VERY cliche. Love the stock photo for #4!

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  • REE REE:

    Everyone wants that moment they tell everyone they are engaged for all to jump up and throw confetti and wish they will live happily ever after. Unfortunately, not all families have read the book on how to react when your daughter/family member and the love of her life announce their engagement. Tell your parents privately and let THEM announce it. It gives them a sense of ownership and prevents YOU from getting hurt if they don’t have the appropriate reaction. Oh, and congratulations!!!

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