The office is buzzing with excitement as Valentine’s Day approaches. If you’re just another single spending Valentine’s Day, then scroll away.
However, if you have planned your first date for 14 February 2026, be prepared to look out for these major icks.
Date Outfit
When it comes to dates, most people stress over what to wear—a printed shirt or a plain tee, skirts or dresses, the jitters are real. However, Natalie and Nicole faced a different dilemma altogether, where their dates turned up in something truly questionable.
Natalie: Slippers, slides, tank top and running shorts—either army shorts or FBT shorts. Unless we’re going to the hawker centre, where I feel only Crocs are acceptable. If we’re going to a shopping mall like ION Orchard or 313@somerset, and he turns up in slippers, jeans and the green army dri-fit T-shirt? I’m turning back home!
Nicole: If they appear in a two-piece outfit that combines to create one full design, it feels like they could’ve put in more effort to look presentable and clean.
First Date Activities
Choosing the right date idea matters, especially when your date isn’t into certain activities. For Vanessa and Jae, things went off-plan, so they had to improvise on the spot—and swore there wouldn’t be a next date.
Vanessa: Nothing was planned, other than a general location to meet later that evening. I updated him that I was going to a cafe with a friend beforehand. Towards the meeting time, he suggested some date activities that include cycling, and gymming! At that point in time, I didn’t pre-pack my gym stuff before heading to the cafe. His suggestions threw me off, because I wasn’t comfortable going to the gym on a first date.
Jae: Our schedules were constantly clashing, but we managed to agree on a picnic slash cycling hangout at East Coast Park. When we met up, he turned up in dress shoes, formal pants, and a polo shirt. Apparently, he forgot that we were going to the beach and assumed we were heading to the National Museum of Singapore.
I was so mortified that I dragged us to Uniqlo to find a last-minute dress that was at least appropriate. There’s no way I would enter a museum in shorts, singlets and sports shoes!
Initiative
Many women appreciate feeling taken care of, especially when a date takes the initiative—whether it’s planning the outing or making decisions. Unfortunately, Natalie and Vanessa experienced the exact opposite.
Natalie: When the guy doesn’t plan for dates and relies on me to take the initiative. Sometimes, when I do end up suggesting date activities that would keep us entertained, we still end up doing what he wants. It’s still fun, but I wish he could’ve acknowledged my efforts too.
Vanessa: When we met at the beginning of the date, he had his arms open, expecting a hug from me, which threw me off, because this was our first time meeting. After we ate, we were chatting away at one of those seating areas like Funan’s steps beside McDonald’s. While we were chatting, he would randomly pat my head or touch my hair. Again, this was still our first date, and I barely knew him for two hours!
Mannerism
A date’s mannerisms often leave the strongest impression, as they reflect a person’s habits and character. Unfortunately, Ash, Yan, Chey and Nicole encountered some questionable ones.
Ash: When her phone is always face-up and buzzing with notifications, and she goes on about her social media activities. It makes me feel like I’m mentally competing with Instagram, especially when I’m physically right there with her on a first date.
Nicole: If they don’t know that there’s mucus flowing down their nose, it’s the same disgusted feeling I get whenever I see something stuck in between their teeth.
Chey: There was this guy I was seeing for a month, who happens to be a narcissistic and egotistical guy. He was claiming that every girl we bumped into was looking at him. Another thing he did was tell me unsolicited stories about himself and his exes, which felt uncalled for.
Yan: I went out with this textbook-perfect guy who was tall, handsome, smart, and sporty. We were out on our third date, and he was laughing at all my jokes because I’m such a funny girl, but then he started covering his mouth with his hand every time he laughed.
The ick hit me like a tow truck—it was wild, because I’m usually very forgiving at the dating stage, and I had no clue why that action turned me off so badly.
We hope our personal experiences help you trust your instincts on your upcoming Valentine’s date. P.S. —icks are subjective; what matters most is having fun and enjoying the moment.
For more lifestyle updates like this, subscribe to our Telegram channel at @confirmgood.
Photo by Jae-Eryana Fitri.
