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15 Disastrous Asking Out Fails That Will Make You Cringe So Hard

By: In: Lifestyle

Relationships can be wonderful when you find the right person. However, there are some steps involved in getting to that happy, secure place with someone. Before it all begins, someone has to bite the bullet so to speak and ask out the other person. Most of the time a simple question will suffice, but if it’s someone really special, you may want to step it up a notch. After all, the more elaborate the proposal, the less likely that person will turn you down, right? That’s not always the case, though, and even if your crush does agree to go out, you still may need to work on your asking game. So next time you’re pining over when and how to ask someone out, just take a look at some of these asking out fails. Whether they failed to get a date or just failed at the entire concept of what is acceptable, these people are sure to make you feel better about your own asking out skills.

15. Because she’ll eventually have to go

Via: mmmarshallll/Instagram.com

Via: mmmarshallll/Instagram.com

If you’re a little on the shy side, one of the best ways to ask out someone you really like would be to leave him or her note. Of course, you would want to leave the note somewhere that person would go so that he or she will be sure to see it. Why not the bathroom? That’s one place every person is sure to visit at least once a day. To make sure she wouldn’t miss what he was asking, he placed a “prom” sign on the toilet seat. He also gave her a bouquet of roses to try and make up for this weirdness. The only way this could get any worse would be if he were to leave her candy, cookies, or some other kind of food instead. Apparently, it worked though. If you read her posting, she gave this moment hashtags that included “clever” and “special.”

14. When you burn for her

Via: buzzfeed.com

Via: buzzfeed.com

You’ve had your eyes on her for some time now, but you’re having a hard time putting those feelings into words. How could you possibly convey how your heart burns for her? This guy thought it would be best to literally show how his heart burns through his chest (and back) for her, and chose to use just one word to do so. There’s no doubt he got his point across, but it turned out being more painful than he ever could have anticipated. It would have hurt him a lot less in the long run to simply say or write what he was feeling, even if it did come out in just one word. He may have scored a date for the prom, but he also scored a case of second degree sunburn and possible melanoma.

13. You’re sneaky, she’s stupid

Via: pinterest.com

Via: pinterest.com

Whenever a guy and girl become really good friends, it’s almost inevitable that at least one of them will begin to see the other as a potential love interest. Before too long, something will need to be said or else you could fall hard and then fall even harder if it ends in rejection. This guy was trying to let his friend know he had fallen in love with her. Unfortunately, he picked a girl who recently fell on her head…or at least who acts like she did. He came up with a sly way of leading into telling her that he loved her. They must be super close friends, because she got the right message but in the wrong context. Even after he tried to clarify what he really meant, she still didn’t get it. Maybe he should take this as a sign to go for someone smarter.

12. What are the odds?

Via: ifunny.co

Via: ifunny.co

It must be pretty common for a guy to ask his girl friend (as in, a friend who’s a girl) for advice on asking someone out when he really intends on asking her. Most of the time she will eventually catch on to the fact that it is her, which was his intention all along. Unlike the previous girl, this one caught on, but only after she had talked her friend up that he would surely not get rejected. She was so confident he would score a date that she bet him $10 the girl would say “yes.” That is, until she found out she was the girl. Then, she wasted no time letting him know he wasn’t her type. But kudos to the guy for sticking it back to her saying that she now owed him $10. At least he got something out of it.

11. That’s what she said

Via: thefunnyplanet.com

Via: thefunnyplanet.com

You could go with the vague approach of asking your love interest for advice on how to ask out your love interest, only to later reveal that it is her. Or, you could get right to the point and just ask. But what if she says “no”? Then you need to come up with a response. This guy had a smooth way of tricking the girl into asking him out. All he had to do was ask her to repeat the question. She probably thought he wanted to make sure she knew what he was asking, but instead he took it as a way of getting her to ask him. Of course, he said “yes.” This could end one of two ways. Either she is amused and agrees to go out with him anyway, or she just gets mad and comes back with a more definite “no.” If only we knew the outcome.

10. Facing defeat

Via: ifunny.co

Via: ifunny.co

Here we see another “promposal,” AKA a bored teenager’s way of making a big deal out of asking someone to prom. This trend can range from a simple sign (on a toilet seat, nonetheless) to elaborate displays of affection. This guy decided to spell it out, while still letting his mouth do all the talking. His promposal may look a little weird, but if a girl likes a guy, she should see it as flattering regardless of how lame it really is. For example, the girl who gushed about the toilet seat promposal. This girl wasn’t flattered though, and she had no trouble answering him back in the same manner he asked her. Maybe he should have thought this through ahead of time and anticipated that she might respond in this manner. After all, there is no “O” in “yes.”

9. The road to rejection

Via: dumpaday.com

Via: dumpaday.com

Vandalism is never good practice, regardless of whether you think you’re supporting a cause or showing your admiration for someone. That’s why few people are proud to have love declared for them on a road sign or bridge overpass. At least most people write the name of someone who loves them back. This guy took a big chance by using a can of spray paint to ask a girl to prom on a bridge. Much like the girl who received the open mouth promposal, this girl was not amused. She didn’t care for him asking her to prom, much less him asking her so publicly in an illegal way. Yet, she had no trouble committing a crime of her own by spray painting “no” beside his question. Now everyone traveling that route will see his rejection in big red letters.

8. Wrong answer

Via: onsizzle.com

Via: onsizzle.com

If you thought the guy who tricked his friend into sending him a text asking him out was slick, then you’ll really appreciate what this guy came up with to ensure he would get a “yes.” He employed the tactics of the age old check “yes” or “no” note but gave it a twist to make sure she chose yes. The joke was on him though, as Katie found a way around his set-up to circle either “yes” or “definitely yes.” He instructed her to “circle her answer,” so Katie found the letters “N” and “O” next to one another and went for it. Next time (if there is a next time after that harsh rejection), this guy will have to find a better way to ensure the girl chooses yes. He did succeed at one thing, though—making the text guy look smart.

7. Thanks for the cheese

Via: thechive.com

Via: thechive.com

If you know your promposal is a little nerdy, then you may as well go ahead and claim it. This guy wasn’t the least bit ashamed to admit that his promposal was cheesy and the intentional pun made it even worse. Luckily for him, the girl didn’t make fun of his cheesy way of asking her to prom by giving her a pizza. Though he would have probably not minded her making fun if he had scored a date in the process. Unfortunately, while she appreciated the gesture—and especially the food—she still had no trouble turning him down. Now, not only is he without a prom date, but he also bought her dinner with nothing in return. The least she could have done was save a piece for him. Oh well, lesson learned the hard way.

6. Appreciate the honesty

Via: lotsofhumor.com

Via: lotsofhumor.com

Here we have yet another poor soul attempting to trick his friend into giving advice on asking out a girl, unbeknownst to her that she is the girl he has in mind. She let him know that simply saying he liked her and getting right to the point was the way to go. She even went as far as to say that the girl would appreciate his honesty if he just came out and said it. So he took her advice and turned right around and asked her out. She obviously does appreciate honesty—on both ends of a conversation, since she had no trouble telling him “no.” If only we could see the rest of this conversation to know if he appreciates honesty as much as she does.

5. Quality verses quantity

Via: whisper.sh

Via: whisper.sh

Sometimes, when you really like a girl, a huge act of bravery is the best way to impress her. After all, who could say no to such a public display of expression (unless you’re Meg and your name is spray painted on a bridge overpass)? But most girls would be greatly impressed by a guy jumping on stage, grabbing a microphone and asking her out in front of hundreds of others. Sadly, this guy chose a girl who isn’t that easily impressed. She turned him down. However, four other girls there told him they would go out with him. Now, he has a decision to make. Will he pine over the girl he really wanted to take out, or will he count his losses and move on to one of the other girls who were impressed by his bravery?

4. Tell her with tobacco

Via: @DipLife_/Twitter.com; Via: indulgy.com

Via: @DipLife_/Twitter.com; Via: indulgy.com

If you’re looking for a unique way to ask someone to prom, you can always go this route. It might just be effective if your girl is, well, a bit trashy. These two guys decided to give it a shot by using tobacco to sway the ladies. Not vape pens or anything like that, either. Just good old-fashioned dip and Marlboro cigarettes. The guy with the dip must be into tough chicks, because he asked her to “take a pinch” to accept his offer. The other guy already knows that his girl fancies tobacco, especially more than flowers. Somehow he thought giving her a pack of cigarettes was a romantic gesture. Something tells us that a girl like that might just smoke the whole pack and then turn him down (kind of like the chick who ate the pizza, but with a trashy twist).

3. High on love

Via: collegehumor.com.au

Via: collegehumor.com.au

If this guy’s eyes look glazed over, it’s hard to tell why. It could be because he just scored a prom date, or it could be because he has smoked a little something to get up the courage to ask her. Either way, she seemed to agree that they would have a high time at the prom together. He even put her flowers in a bong to make sure she had what was needed to ensure the night would go as planned. How thoughtful of him! We’re not really sure where these kids go to high school or what kind of rules they have at the prom (or lack thereof), but chances are they either live in Colorado or out on the West Coast. That’s just how they roll in those areas.

2. Memories that last forever

Via: ifunny.co

Via: ifunny.co

Prom is one of those rites of passage in everyone’s life that will create memories to last a lifetime. That’s why when you’re a teenager, it can seem like such a big deal and the most important thing in life. Still, it’s important to remember that prom will not be the most important thing forever and the only thing likely to last past that night is the memories. Sure, some select people might end up marrying their prom dates, but that’s highly unlikely. This guy was determined to make sure something besides pictures lasted from his prom, as he actually had the word “prom” tattooed on his side. Luckily, she said “yes.” It’s already bad enough that he will be stuck with such a stupid tattoo forever. Imagine explaining that one to your future children!

1. Prom’s the bomb!

Via: columbian.com

Via: columbian.com

Possibly the worst luck a guy could have would be to ask out a girl and have her say “yes,” only to miss out on the date due to a technicality. In this guy’s case, he was the technicality and it was all his fault. For some reason, he thought it would be cool to strap a fake bomb to his body and ask a girl to the prom by saying he’s “the bomb.” While Rilea seemed to agree he was the bomb since she agreed to go to prom, a lot of other people thought he was a bomb as well. This included the school district, who decided to give him a suspension from school classes and events. That would include a suspension from the very prom that he had just asked Rilea to attend with him. He really bombed that one! How’s that for irony?