From The Straits Times    |

 

I recently started dating again after ending a long-term relationship

last year. After five months out of the game, I quickly found I had to relearn many of its rules. The first: Who pays on the first date? On hindsight, I should’ve asked around first. Unfortunately, I tend to adopt a “just do; don’t overthink it” mentality, which often leaves me in situations where I have to learn from experience.

 

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Date 1

 

The conversation flowed smoothly; M and I had quite a bit in common in terms of career decisions and personal interests. Going well, I thought. Definitely want to see her again.

When the bill arrived, I was all set to pay. But M threw a spanner in the works, saying: “Hey, I don’t have cash – let me pay by card.”

 

Before my brain could process what was happening, I blurted out: “Er, okay?” M gave me a squinty, sideways glance and primly placed her piece of plastic in the bill folder. Five seconds later, it hit me like a Ferrari running a red light at Rochor Road: Oh my gosh! I wasn’t supposed

to let her pay! I tried giving her more than my share because I didn’t want to seem like the cheapskate that she probably thought I was. She politely refused and signed the bill as though she were signing a death warrant – on future dates, that is.

 

 

Date 2

 

I must confess: I forgot her name, so I’m using H… for Help. It was one of the most mind numbing outings I’d ever been on, hence my inability to recall her name. But like the gentleman I was raised to be, I stuck it out for one and a half hours without so much as contemplating an escape plan.

 

When she finished her drink, I dutifully asked if she would like another. “No,” she replied. “It’s getting late – let’s make a move.” “Sure,” I said. “I’ll ask for the bill.” As I waved to the waiter for the cheque, H excused herself. That’s fine, I reckoned. The call of nature seldom comes at a convenient time. The bill, however, came immediately. So I signed for it. Then I waited. And waited. Ten more minutes passed in the almost-empty bar and I was just about to ask the wait staff to check on her when H reappeared, looking as chipper as a chipmunk on a chestnut farm.

 

“Thanks for the drink,” she chirruped. “Shall we go?” Huh? Wasn’t she even going to

attempt the cheque dance? Nope. H blithely skipped away, taking with her any remaining thoughts I had about asking her out again.

 

Date 3

 

It was a dinner with X and Y. Th is wasn’t a threesome. Y is a buddy who always uses me as his “alibi” when convincing his fiancee to let him join us on boys’ nights out. So perhaps it was guilt – or pity – that prompted him to arrange dinner with X (his female friend) and me.

But just before I left my house that evening, I realised that, hey, this was a set-up. Which meant it wasn’t exactly a first date! In that case, what were the rules when it came to getting

the bill? I texted four close female friends and got a 50-50 conclusion. Two women said: “Pay for her.” The other two said: “Split the bill – you guys are going out as friends.”

 

Clearly, crowdsourcing had its limitations, so I was on my own with nothing for comfort except these two conflicting sentiments: X and I were going out as friends – and what if I didn’t want to see her again, a la H from Date #02? But what if I wanted to see X again? Wouldn’t I seem cheap if I asked for her share? After five minutes, my decisive instincts kicked in. I texted Y: “Bro, you get the bill later. Ask X for her share; I’ll transfer mine to you after dinner. Less awkward this way. Thanks.”

 

Problem solved? Nope. As it turns out, Y called for the bill – but it came to me instead.

They say experience is a brutal teacher. It is – I coolly signed the bill, telling Y he could square accounts with me via Internet transfer. Good on X for offering to pay, though I didn’t take her money. I didn’t know if I wanted to see her again, but I thought I’d err on the side of caution.

 

 

In any case, ladies, if there’s something to take away from my experience, it’s this: The next time you’re out on a first date, offer to pay your share. It’s the polite thing to do. If he waves away your offer and you want to see him again, suggest post-dinner dessert or drinks – on you. If there’s a “matchmaker” present, let him or her handle all money matters, from paying the bill to collecting everyone’s share. Above all, remember to enjoy yourself on that possibly magical first date. So put yourself out there and have fun – but don’t forget to do the cheque dance.

 

This story first appeared on Herworld print edition, May 2013.