Win A $300 Experience Voucher For Valentine's Day

We've already offered some suggestions on buying the right Valentine's Day gift, but if you win this competition, your problems are solved. One lucky ready will score a $300 voucher from Red Balloon, which you can spend on any experience offered through the site.

This competition runs for just 24 hours, and we'll email the voucher to the lucky winner straight away, so you can still use it as your main gift on Valentine's Day — and even redeem it for the ideal gift experience if you want. (We won't tell if you don't.)

To enter, just tell us in the comments about your worst-ever romantic experience. The one we find most amusing (or harrowing) wins the prize. Full terms and conditions here. Get searching and get commenting!


    A few years ago, I wasn't having much (well, any) luck with the ladies, for quite a long time. I realised that I needed help.

    So I asked my long time friend/housemate for advice about asking out this girl that I was pretty much falling for at the time. He suggested this nice local Teppanyaki restaurant. I asked her and, what do you know, she actually thought it might be a fun date!

    The day rolled around, I was getting psyched to take her out for dinner that night, and she called me to cancel. "Oh well," I thought. She had a reasonable excuse, and I figured that if she was interested in going out with me this time, surely we could reschedule?

    Apparently not.

    I tried rescheduling, I tried coming up with other ideas, but she kept turning down any further offers. Not long after that, she got back together with the man that she broke up with almost a year beforehand, and about a year later, they got married.

    I still don't know what I did wrong.

    To cut a long story short, try imagining setting up a bed with candles and rose pedals, stark naked and your mum (who has a key) coming over before your girlfriend does! Still haunts me to this day.

    I when't to ask a girl i'd been interested in a while out. not only did i get friend zoned while trying but she then asked for advice on how to ask someone else out.

    I whent to ask a girl i’d been interested in a while out. not only did i get friend zoned while trying but she then asked for advice on how to ask someone else out.

    I went to ask a girl i’d been interested in a while out. not only did i get friend zoned while trying but she then asked for advice on how to ask someone else out.

    Since New Years Eve, I'm supposed to be back in a relationship with my ex-boyfriend. He came back and said that he's leaving the girl (that he still had over while we were together) because he can't see himself marrying and having kids/a future like that with her). So stupidly enough I thought that the 3 and a half years apart (dating her) and with his new approach to me and him that things had in fact changed. Two months later and I'm still waiting for this girl to stop sleeping in the same bed as him and find her own place to leave. He refuses to kick her out or make her sleep on the couch because he "still gets along really well with her" and see's no point in making problems that are avoidable between them - and wants to have her as a close friend still. He lives in Sydney and I live in Queensland by the way, so I only get to spend the weekends with him whilst she gets to be there every day of the week. It's the day before Valentines day and I can't be in Sydney with him. I KNOW that he's going to spend Valentines day with her because I asked him about it and his reply was "I'm not going to say no if she's got somewhere nice booked and asks me to go". He won't even change his facebook status from being in a relationship with her to being in a relationship with me. That and this one guy has never bought me a birthday/anniversary present. And on every birthday THUS far has made me cry.

    Blergh, I'm going to leave it at that.

    Someone explain to me why I love him?

    I went on a first date with this girl I really liked (and naturally because I really liked her, I was incredibly nervous).
    We went to see a movie and I was too nervous to try anything like hold her hand, put my hand on her knee or anything like that until about halfway through. I went to put my arm around her shoulder but I did it too quickly and punched her in the face. She screamed and started to cry and everyone around us thought I was hurting her. She ran out and I was left with a face as red as a beetroot.
    She called the next day to tell me she didn't want to see me again. I noticed she had a slight lisp on the phone and I stupidly asked her what was wrong with her voice and she started screaming and swearing at me, telling me I had hit her so hard that I had bruised her cheek to the point that she coulidn't talk properly. Worst. Date. Ever

      This actually made me laugh out loud. I feel for you buddy!

    Some years ago in Canada I had a job at a ski resort and for good performance I was given 2 lift passes. I asked my girlfriend at the time (admittedly, things weren't going as well and the writing was on the wall) whether she would like to accompany me skiing for valentines day. Her response was an unenthusiasic, 'meh'. My response was to invite out a very pretty german girl I'd recently been introduced sense wasting the lift pass. As fate would have it, my soon to be ex girlfriend decided that she would in fact go skiing that day and surprise me...and wasn't I surprised to be busted skiing with another girl! I was 15 or 16 at the time and it was the only time I'd ever, sort of, cheated and got caught red handed. Not cheating by today's standards I'm sure but I learnt my lesson.

    It was probably only a month or so into our relationship. I was suave. I was cool. I was, let's be honest - more experienced with her in relationships and had a bunch of tricks and impressive feats up my sleeve.

    And then... well that happened.

    We had met her at work and I fell hopelessly for her - had a crush brewing for her for months. In fact, I think everybody knew. It was hard not to. I'm a pretty confident, happy go lucky guy, but around her... I was a mess.

    Eventually I asked her out, we went on a few dates and had a great time. Things were going really well. I had put to use all my experience in wooing girls for this one. My game was perfect - it had to be.I was, to be honest, in love with her in probably the first few weeks.

    I had also bragged about my culinary skills. I'm a pretty darn good cook thanks to a mum who insisted I learn as a teenager. So I eventually planned a big night and made a tasty meal of Turkish chicken burgers and caramelized peaches.

    Things went well. She loved it. We laughed, ate and had a great night.

    And then... I started to feel a little off. A little green. I couldn't sleep and my stomach was starting to cramp up. A few hours later and it was midnight, with me sweating like a pig, trying not to groan too loudly and wake her up.

    Cut to three am and it felt like Obi Wan and Darth were saberin' up and down my belly. I couldn't stop shivering. I ended up running a hot bath and sitting in it, huddled up like a big, fleshy pretzel. The girl came and checked on me, but 'I was fine' I insisted. 'Just fine'.

    Reluctantly she left me to go back to bed (she did have work in the morning)... but, as soon as the door closed I felt it. Something I had never felt before yet knew unmistakably what it was. Like somebody knuckle dustered my stomach.

    Oh god. No. I had never vomited before in my life and then. I stood up and for some insticinctive reason turned to the sink and BOOM! Shotgunned vomit all over the mirror, vanity and filled up the sink.

    Jesus it was horrible. Chunky, half-digested peices of bread and chicken and peaches.

    And poor Girl, she walked right back in, looked me up and down, standing naked and dripping vomit and immediately got to work picking the chunks out of the sink drain.

    She cleaned everything up (including me), rolled me into bed and looked after me like a nurse for the rest of the week.

    It was the most horrible, disgusting and lovely thing I had ever experienced.

    And I still love her for it.

    I once went on a date with a lovely girl to a nice popular restaurant in the city. We had plenty of fun and the food was great, she picked it and said her parents went quite often. Low and behold, her parents show up and we exchanged pleasantries, which wasn't awkward at all and her parents seemed very happy. After what I thought was a fantastic evening, she tells me that the whole thing was a set up to prove to her parents that she wasn't batting for the other team. Turns out, and unbeknownst to me - she was and already had a girlfriend.

    I met a girl online years ago and we spoke a few times via chat/phone before meeting face to face.

    We had a drink, pub dinner, then played pool (plenty of cliche "I'll show you how to play" moments) and then sat down for a few drinks. She turns to me and asks if I believe in fairies. Straight faced and she kept pushing until I agreed.

    As we're leaving she kisses me and says we should catch up again tomorrow, she'd love to spend more time together but has to collect her sister from some kind of training. I say goodbye, she leaves.

    And then she sends me an SMS not 5 minutes later saying "I'm so sorry I've thought about it and can never be with someone who doesn't truly believe. Don't call me again".

    We went to what seemed like a lovely Italian restaurant in Pyrmont.
    Their chef's cooking was awful. It was strange and tasted off and had pile of oil. Inedible.
    We sent it back - - rather than a refund, they attempted to 'fix' it.
    And then charged us twice. (It was the same plate!)

    Away we went, hungry and angry. To what better, than the food court in Harbourside and some greasy greasy KFC. Isn't it funny when the KFC was less oily than the pasta? (Although much more hairy?)

    We had also booked the Sydney Observatory for a night tour.
    It rained heavily and the giant telescope was shut off.


    Once went on a date with a girl who turned out to be a guy. Whoops.

    Took a girl on a first date to the movies many years ago. Turns out that feminists don't have a sense of humour especially with a film like The Adventures of Ford Fairlane. How was I to know that was the definition sexist, I was only 16 at the time.

    Anyway I laughed my arse off and she stopped shaving her armpits and turned lesbian. At least I had a good time.

    Everyone is thinking it, so I'm going to ask. Has the comp been judged yet? Has the prize been awarded?

      I once entered a Valentines competition which was to be drawn on Valentines day, the entries were meant to be reminiscant of your worst Valentines day...well, today is the day and all I'm left with is a handful of heart breaking memories and no prize. Thanks Lifehacker.


    Feeling queasy on our first date. My Tummy rumbled, followed by a few silent yet deadly gas bursts , then whoosh!!!! A wet fart!!! As I bolted to the bathroom, my heel got caught and tangled on a diners handbag strap (which was on the floor), I lost my footing, and sprained my leg. And guess what???? My date actually saw me again!!!! I call him hubby now.

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