The season of love is upon us again and for all those lovebirds out there, that would mean another all-important Valentine’s date that you cannot mess up. While you may have the perfect night already planned out, there’s always the possibility of it not turning out the way you want it to. Here are 14 real-life accounts of romantic dates that turned a special day into an awkward, infuriating and embarrassing event they can’t forget.
1. A Romantic Date That Ended in Flames
“This was the first Valentine’s Day I celebrated with my boyfriend of three years. At the time, we were broke JC students so we agreed not to go out to celebrate and I went over to his place for dinner instead. Dinner was fantastic and everything was so romantic and on point. But then, after our meal, at the table, he reached over to touch my face and accidentally knocked a candle over and my hair caught fire. I didn’t know if my hairspray had anything to do with it but it was disastrous. On the bright side, I had been meaning to try a pixie cut anyway.”— Anonymous Singaporean
What we learned here: Even though it’s a date, always be aware of the potential fire hazards around you.
2. Is Today Valentine’s Day?
“I was casually seeing a guy for a few weeks and wasn’t sure if I wanted to get more serious. Then, he asked me out on Valentine’s Day, and I was flattered. I thought, ‘He must be ready to take our relationship to the next level’. When we got to the restaurant, we sat down, and a waiter handed us the special prix-fixe menu. My date asked, ‘Oh, is it Valentine’s Day?’ and I nodded. He seemed genuinely shocked and even had the nerve to tell me that he wouldn’t have asked me out if he had known what day it was!” — Meredith
What we learned here: Ensure your potential date knows the important days of the year before making plans.
3. Started as a Couple, Ending as Friends
“A new guy surprised me by planning the perfect Valentine’s Day date: a romantic dinner followed by a fireworks show on the beach. Everything had been going great until the check arrived. He asked me, ‘Should we split it, or do you just want to pay for your meal?’ After dinner, we took a walk on the pier where we bumped into a girl, who looked like his ex-girlfriend. They were talking and laughing with each other for about 20 minutes until he finally said, ‘Oh sorry, this is my friend Kat.’ Of course, we broke up the next day.” — Katrina
What we learned here: If your partner wants to go dutch on Valentine’s Day, don’t even bother attending the second half of his presentation.
4. Happy Valentine’s Day, Let’s Break Up
“My now ex-boyfriend had invited me over to his house to spend Valentine’s Day with him. I was really excited, and I had even bought him some really nice pens and a notebook because he was really into drawing. I drove 30 minutes from my place to get there where we were just hanging out in his room. While we were together, he was acting really weird so I asked him what was wrong, and he proceeded to break-up with me right there, after I gave him his present.” — Shanna
What we learned here: When your other half starts acting weird, it’s always nothing good.
5. Here’s a Gift Meant For My Ex
“I got a stuffed dog and a sweet, heartfelt declaration of undying love… that was written for the guy that she had just broken up with in order to be with me. She just figured screw it, it’s already written and sealed. She even scratched his name off the envelope and wrote mine. We obviously didn’t last long.” — Bowyer-Betty
What we learned here: Don’t be the second choice.
6. An Unexpected Confession That Ruined The Surprise
“Last year, I wanted to mess with my girlfriend on Valentine’s Day so I planned a surprise for her with a few of her close friends. The plan was for me to ask her out then bail on her last minute with me ‘forgetting’ that it was Valentine’s Day. Her group of friends would then ask her out and lead her to me. I don’t cook but in order to surprise her, I went and learned a few recipes as well as a song on the guitar.
On Valentine’s Day, everything had gone as planned. I had spent the day preparing everything for the evening with her. She had been adequately upset and her friends were also pretending to be upset at me. But then, unknown to us, one of her guy friends confessed his feelings for her! Luckily for me, even though my girlfriend had thought I was being an asshole, she still told him that she was happy with me. Needless to say, he got so upset that he bombed the surprise.” — Anonymous Singaporean
What we learned here: Always factor in the possibility of potential suitors waiting for you to slip up (even if it’s just pretend).
7. When Your Other Half Sleeps Through V-Day
“I made reservations for my boyfriend and myself to go to a hotel that was doing dinner and a movie. He was supposed to text me when he woke up from his nap and was getting ready, but he never did. Eventually, the event was about to start, and I was still at home. I had to call and cancel. He called me an hour later to tell me he overslept. I cried.” — Elizabeth
What we learned here: Never forget that your phone alarm is your best friend.
8. What Not to Do Even on a Boring Date
“I witnessed a girl fall asleep on her date. At first, I thought she was simply mocking her boyfriend by resting her head on her chin with her eyes closed. But after some time had passed, it was apparent that she was legitimately asleep. I watched her date throw money on the table and briskly walked out. It was probably more rude than awkward. I blame the hip, low-lit ambience and comfy oversized chairs.” — Gabrielle
What we learned here: Either make up an excuse to get out of the situation, or invest in those eyeglasses with fake eyes for lenses.
9. Who Cares For Your Grand Romantic Gesture?
“I got a hot-air balloon for my girlfriend, and she hated it. We went up for about 10 minutes and she yelled, ‘Take me down, I hate this.’ She broke up with me as soon as we got to the bottom. I still had to pay in full. It was $150. For 10 minutes.” — Kameron
What we learned here: Always get your money’s worth — don’t shortchange yourself!
10. Happy Valentine’s Day Mum!
“I had recently started dating my boyfriend at the time a week before Valentine’s. Although we hadn’t made plans on Valentine’s since it was a weekday and we both had after-school activities, I had assumed he would do something to surprise me.
Later that day, my mum said that she had found a red rose on her car. She had a secret admirer but we couldn’t figure out who it was. After ignoring my boyfriend for his lack of surprise on Valentine’s Day, he asked if I received the red rose he had placed on my car — the car that me and my mum shared. I apologised to my boyfriend for being rude and never told my mom the truth. To this day, she still doesn’t know who the admirer was.” — Nicole
What we learned here: If your man can make your mum smile, he’s a keeper!
11. Wow, That’s So Useful
“I’d been going out with my boyfriend for a few months and it was going great. I was really excited about our first Valentine’s together until he presented me with my present — a wrench. His explanation? ‘Well, everyone needs one for their car, don’t they? I thought it’d come in handy.'” — Leanne
What guys should learn from here: Yes, women do like the occasional impractical gifts on Valentine’s Day.
12. Went on a Date Which Turned Into a Lecture
“I didn’t really think of Valentine’s Day as an important date so I agreed to go out with a guy I just met through Tinder. Instead of a nice date, I got judged for getting a cup of Thai Milk Tea because he felt that I was wasting money and not saving for my future BTO. When I told him that it was only possible to get his own flat if he was still single by 35, he got defensive and said he was going to get married before that — Sure bro. As if the constant nagging wasn’t enough, he made me accompany him to NTUC where he bought all of his groceries and left immediately after because he didn’t want to carry them around!” — Hui Ting
What we learned here: At the mention of BTO on the first date, you should immediately GTFO.
13. When Your Other Half Has Long Term Plans For You
“My ex-girlfriend used to make me these special organic meals all the time and said she had a special chocolate recipe for Valentine’s Day. I didn’t like her cooking at all but I did appreciate how much work she put into them. Just before Valentine’s Day, I found this bag of traditional herbal medicine in her kitchen. I read the package and was shocked to find out that it was for male fertility. I confronted her about it immediately and she told me that she wanted to get pregnant so we would have a reason to get married. She had apparently been feeding me these herbs for months but I just didn’t know about it! It obviously didn’t work because I broke up with her that day, moved and changed my number!” — Keigo
What we learned here: Sometimes love makes people crazy passionate.
14. Sent a Sweet Gesture but Ended Up Getting Ghosted
“I’ve played my fair share in the dating culture where ghosting and being ghosted was such a norm. It’s honestly sad to say, but I guess that’s how the scene is like nowadays. However, there was one incident that occurred, about 2 years ago on Valentine’s Day that’s been ingrained in my head.
14 February 2018. I was going out with this guy in my school for at least two months and we were still in that phase of getting to know one another. So of course, as the “big” day dawned upon me, I thought I’d get a small gift for him. And by gift, I meant flowers — now, you must be thinking, why would a girl get flowers for a guy? It was 2018, times have changed — get with the programme.
Anyway, over at school, we had a Valentine’s Day drive where they sold roses to give to your crush or even to that sad single friend of yours. The catch — there was also a secret Valentine option for us to send flowers to your Valentine directly to his/her class. And obviously I went for the latter because I’ve always liked that element of surprise.
Fast forward to the part when it was delivered, my date texted me, asking if I sent him flowers and I admitted to it. Now you might think he’d appreciate the gift or even the mere thought of it, but shockingly, he was taken aback by the whole idea of it. In fact, he started being cold towards me and he ghosted me a few days after. His main reason? He wasn’t ready for the dating scene. A ridiculous excuse? Sounds more like an understatement to me.” — Charlene
What we learned from here: Don’t ghost anyone you’ve been seeing, or you’ll end up as a cautionary tale on Valentine’s Day.
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