My Worst First Date: “Getting to know all about my Valentine’s ex-wife”

Her spontaneous date with this man just shows that sometimes it’s better to be alone on Valentine’s Day.

My Worst First Date: “Getting to know all about my Valentine’s ex-wife”


It wasn’t my intention to initiate anything on Valentine’s Day. I just happened to be on my way home from the gym and I was bored. So I ventured on to Tinder and stumbled upon Asher’s profile. Ordinarily, I would wait for the man to text me first, but that day I decided to shake things up by starting the conversation.

Asher responded almost immediately. His replies were funny and we hit it off. We texted back and forth for about 15 minutes before he asked me to meet him that very night.

On Valentine’s Day? Really? I was sceptical but he was very persistent. “Be spontaneous” he told me, pushing me to enjoy a drink with him. After I rejected him the first five times, I finally relented when he agreed to meet me somewhere near my home (believe me, changing out of my pyjamas took way too much effort as it was).

One look was all I needed to know I wasn't keen. Asher looked nothing like his picture, and not in a good way. Photoshop has a lot to answer for. We got a table at the restaurant and I quickly ordered myself a glass of was required to get myself through this date. The conversation was a little stiff at the beginning, which I understand is pretty normal for a first date. I asked him about his life and that’s when he started to drop hints about his backstory.  That was my first mistake right there.

He began with the banal facts: He’d moved to Singapore three weeks ago from Texas, “but it's a long story” was how he finished that one off. Oh, okay then. He then told me he had a huge scar because he got into an accident – another “long story” apparently. This went on for a while until it became clear he wanted me to ask him to elaborate on this story behind all the little things he was sharing.

So, I obliged. He launched into a detailed explanation of why he moved here. He was trying to escape his life, the person he’d become been ever since he got married and his ex-wife who was still in the US. Righhhhhttt. I asked him when he got divorced and he said that technically he isn't. He insisted that they were separated since October. From there, he dove into the dramatic story of their life together….

Poor ol’ Asher had been with this woman for many years and over this period they broke up at least 200 times, according to him. One day, he got into a major car accident that nearly ended his life. She didn't visit him for months while he was in recovery. Then she suddenly reappeared in his life and just like that, so they decided to get hitched (how random is this?). “I didn’t love her but what did I have to lose” he told me. (He’s a real gem, this one.) He repeatedly lamented that he only knows how to make stupid decisions in his life. I fought the reflex to roll my eyes.

This man was on a roll now. He introduced yet another character in his tragic tale, a female friend who was in love with him even before he got married. He claimed he never touched her, never cheated, but that she declared she would wait for him, harbouring hope that he will one day leave his wife for her.

My Worst First Date: “Getting to know all about my Valentine’s ex-wife”


“One of the reasons I stayed with my wife for so long was so my friend could find love elsewhere and get married”, Asher explained that he didn't want to be responsible for her holding out her life forever and wanted her to move on. As noble as that sounded, I was getting extremely tired of hearing about his romantic history. I’d survived an hour or so of his rambling and was categorically done, so I stretched deliberately in my seat and mumbled something about having to head to work early the next morning. We hugged goodbye awkwardly.

Later that night, Asher dropped me a text to apologise for dragging me out of the house on Valentine’s Day. That’s when I lost it. I told him he should feel bad because only an insensitive person would talk about his ex-wife on a date. He seemed genuinely shocked. He explained that he’d felt so comfortable with me and liking me so much he wanted to share his life story with me. Yeah, right. I said I didn’t want to hear from him ever. Again.
“Please meet me in person so I can properly apologise” he pleaded. I rejected him, beseeched him to leave me alone and blocked him on all social media platforms.

Don’t feel bad for Asher, though, because now he has one more sob story to tell his future dates.                   

-Hannah*, 27
*Names have been changed.

READ MORE: TRUE STORY: "He was lying to me long before we got married." and My Worst First Date: “The $20 Bandit”