updated 21 Jul 2013, 19:00
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Mon, Jan 28, 2013
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7 ways to win a date
by Jeanne Tai

Strategy 1: Chance chat on MRT

You have to be a bit brazen to talk to a guy just about anywhere. I don’t mean flinging yourself at him, but it pays to be a shade more outgoing. And flashing a smile doesn’t hurt.

Just by chance, on Day One of my mission, a boyish-looking guy chats me up on the MRT train. I’m immersed in a new book, a collection of dark stories that satirise well-known fairy tales.

“What’re you reading?” he asks, peering over my shoulder. I tell him it’s by a local author and he probes for details. “Well, um, in Chapter One, Red Riding Hood gets raped by three little pigs,” I say, before realising that I sound deranged.

Thankfully, MRT cutie isn’t fazed and we chat about our favourite authors. Realising a golden opportunity, I let my guard down. Like most reserved Singaporeans, I’m wary when strangers strike up a conversation. But this time, I cock my head to show interest and ask questions. I learn he’s an avid swimmer.

When we get off at the same stop, he asks for my business card and whether I’m on Facebook. For some reason, my reserved side kicks in and I play it cool. I just give him my name, telling him I’m searchable on FB, before walking off.

flop!: He doesn’t add me on Facebook. I kick myself for being so aloof at our parting. Lesson learnt.

Strategy 2: Bffs find me dates

I called seven female pals to set me up with their buddies.

Within two hours, I have three blind dates. I realise I’d never tapped on their social networks before – seems they had cool bachelor friends all this while.

One of the men texts me to arrange a date and we end up chatting over Whatsapp. He’s an articulate 20something doctor. On date night, he picks me up from work. He’s pleasant-looking but not someone I would’ve immediately noticed at a party. I have an inexplicable liking for roguish-looking, bad-boy types. Unfortunately, they usually turn out to be more Charlie Sheen than Johnny Depp – jerks.

Our young doctor, however, is a gentleman, regaling me with funny anecdotes about his work. The night zooms by in a flash.

better luck next time: The fastest way to get dates. I also knew my BFFs wouldn’t set me up with loonies. The young doctor turned out to be better as a friend – the chemistry was missing – but I’m glad I got to know him without prejudgments.

Strategy 3: Having a wingman chat up guys for me

Hitting on guys at a club is not my style, but I decide to try. So, I head down to a popular joint in Clarke Quay with my gregarious pal Y. Tip: If you’re shy, enlist a wing(wo)man like I did. She’ll help you chat up guys and deflect unwanted suitors while you zoom in on your, ahem, prey.

Y quickly eggs me towards a pair of smartly dressed men in their 30s near the bar. “Pretend to bump into them and apologise. Just say something!” she bellows over the music. We walk over to the duo. Y flashes them a smile and chirps, “Sorry, coming through!”, before pausing at the table next to them. With contact initiated, the men chat us up. It turns out they’re pilots. Sexy job, anyone?

After some drinks, we head out for supper. We chat easily and one of them, L, tells me how he ended up flying. We eventually swop numbers and arrange to meet for group drinks.

I’m lucky the guys don’t pull any sleazy moves. In fact, L gives me a lift home – classy.

The next day, a colleague remarks: “Men in uniform – I’m impressed!”

jackpot! (sort of): Our group meetup happens the following week. Over dinner, I soon realise that while L’s a lovely guy, he’s not quite my type. But interestingly enough, he’s hitting it off with Y that evening – so I discreetly leave the two of them to go for drinks alone. It’s my way of paying her back!

Strategy 4: Trying a dating website

I set up an account on Okcupid and complete a basic personality test, so the site can find me suitable “matches”.

I get 13 messages within five days. Most are uninspired – “Hi cutie!” and “How are you?” are common opening lines. Yawn. To my horror, there’s even a message from my ex-boyfriend. The site had gauged us to be a “74 per cent” match and recommended that we connect. “I guess Okcupid doesn’t filter out exes…,” he texts me.

But there is someone promising – an aspiring Singaporean chef working in a Michelin-star restaurant in the US. “I saw you’re a writer and just had to speak to you!” he messages. He’s upbeat and exuberant, and his jokes make me laugh. We progress to Whatsapp conversations and he sends me photos of dishes he’s created – sea bass with poached shrimp and steak with artichoke puree. Well, hello there!

better luck next time: We message over the next four days but it slowly dies down. The time difference makes it hard to keep up, and he won’t be returning to Singapore for months. But I might look him up when he’s back. Perhaps he’ll make me a coq au vin. Yum.

Strategy 5: Testing a dating app

Smartphones can do everything these days – even help you nab a date. At least, that’s the theory. I test it out by downloading Blendr, a dating app that uses your phone’s GPS to pinpoint your location and alerts you to users nearby. You can meet them for coffee or more… But let’s not go there.

I chat with three guys using Blendr’s messaging function. I’m uncomfortable with the app’s anonymity – none of the guys have clear photos nor are they using real names.

I write off two of them after 15 minutes – “wat u doing” and “care 2 b frens?” do not an exciting conversation make. The third guy insists on getting my number. When I decline, he accuses me of being “insincere” and “arrogant”. Annoyed, I sign off.

flop!: My Blendr experiment lasted under an hour. Conclusion? Never again.

Strategy 6: A casual drinks meetup for singles

My friends break into titters whenever the Social Development Network (SDN) is mentioned. Keeping an open mind, I log on to the SDN website. It has a very comprehensive events listing page detailing singles events around town, mostly organised by private dating agencies. I decide to go for a casual drinks meetup over the weekend.

I arrive at the bar and am surprised by the healthy turnout of about 20 men and women each. We’re seated in groups of five to six. After 20 minutes, the men in each group move on to the next table, and so on. That way, we all get to meet each other.

I’m excited to find a fellow scuba diving enthusiast at my table. We chat about dive sites in Malaysia and how we would both love to catch sight of a great white shark – geeky diver talk.

When I reach home, I find four Facebook requests and three more e-mails from guys I met at the event (including the diver). Whoa, not bad.

jackpot!: A great way to meet several men in a sitting – in fact, it can be a little overwhelming. I ignore most of the e-mails and Facebook requests, replying only to the diver. Hey, what are the odds of meeting someone who shares your crazy dream of diving with great whites?

Strategy 7: A double date with friends of a friend

One of my friends asks if I’m open to a double date. Sounds cute. Why not?

We meet for dinner in Tiong Bahru. I have to hand it to her – her friends, Tom* and Paul*, are in their late 20s, good-looking and great conversationalists. How come I never have luck meeting such guys on my own?

There are no awkward moments. My friend knows both guys so there’s an easy rapport between them. It’s a cinch for me to latch onto their conversations.

We finish dinner and I’m about to call it a night when they suggest heading over to a live music venue for drinks. We’re one of the few there and flood the band with song requests. They end up playing our song by star of the moment Carly Rae Jepsen. It’s cheesy, but anything sounds great with beer and good company.

At the end of the night, Paul tells me: “Thanks for being game to meet with total strangers. It was really fun hanging out with you.” Likewise!


It’s Tom who follows up with me. Over the next few weeks, we chat regularly and catch a few movies. It’s too early to predict anything, but I’m happy with how things are going. Is he special? Let’s put it this way: My friend’s already pestering me for a treat. *Not their real names

Trying out the strategies got me thinking. Like many girls, I used to be uncomfortable about putting myself “out there”. But I’ve had a change of heart.

The times I’d played the aloof card, I’d missed out (like MRT cutie). But when I’d been open and spontaneous, I’d been rewarded with surprises – meeting cool pilots, a fellow diver and belting out Carly Rae tunes with two hotties.

So gents, you’ve all got my number.

Call me maybe?

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