How to talk to women in life’s most awkward situations

I remember when I first moved to London at 18 and became close friends with the girl I worked opposite. She was 27, at the time of our first meeting had just broken up with her long-term boyfriend of 5 years and thus was throwing herself head first into the dark and stormy waters we call the dating game. The same game that, at this stage in my life, was very unchartered waters – I had spent the last 7 years of my life trapped within the chastity-belted confines of an all-girls boarding school on top of a hill in the middle of the countryside. Dating was something I knew very little about. My only knowledge of it was through The OC and Sex & the City, which, if we hadn’t got ourselves into too much trouble that week, we were allowed to stay up past ‘lights out’ to watch on a Thursday. News Flash: They’re both bloody unrealistic versions of reality.

We worked in a small art gallery in the middle of Mayfair and would spend hours each day staring through the floor-to-ceiling glass windows out at the passers by. Aside from obscenely wealthy old women parading their small dogs and big diamonds around the square at lunchtime, and the flurry of impeccably dressed school children and their even better dressed nannies at 4pm each afternoon, there wasn’t a great deal to lust over. So when a rather good-looking man caught said friend’s eye one day after pretending to be observing the John Frederick Herring, Jr. in the window, a great love story began.

Awkward Situ - TGJ.01

(Image: Chris Craymer)

Every day for 2 months, said man would walk past and stare at her, occasionally giving a suggestive side-smile. They’d cross paths on the way to Pret at lunch and we’d even see him drinking with friends at the same pub we would go to every Thursday at 6pm – the chemistry was undeniable. Then she got a new job, moved away and they never even had so much as a hello.

The same friend once told me that there was a trend going around the then 20-something London transport scene where men and women who had continued eye contact on public transport would flick their business cards at one another as a passionate act of expressing interest and simultaneously gaining each others details. I can’t say I ever saw this happen, it’s certainly never happened to me, but there is some kind of method to such a madness. Every man and woman I know has a ‘commute crush’ – someone you see almost every morning on your way to work, on the bus or on the tube that we make eye contact with, smile at even, but have never mustered the courage to actually act on. Have you ever said hello? Asked for her number? No. You haven’t have you. Well gents, it’s time to change this.

I’ve said it once and I’ll say it again. No woman is ever not flattered by being asked out. Simple as that. From the tube to the bar, here are 5 ways you can start talking to women in life’s more awkward situations this week and I strongly counsel you to keep this mind.


Transport - tgj

Before you start sending in desperate pleas to Rush Hour Crush at the Metro, ask yourself this: has your tube crush ever looked at you like you’ve looked at her? If yes, then she’s probably the same girl that walks into work each morning and tells her colleagues with frustration about the good looking guy she sees every morning on the same commute. Do not loudly ask her out in front of fellow commuters, it’ll embarrass her. Instead, start building up a rapport – one day start with a smile, the next a “good morning” and before you know it you’ll be able to quietly ask her if she fancies a drink sometime. Hand her your number subtly (again, no one wants to be embarrassed pre-9am in the morning) and leave it in her hands.


Gym - TGJ

(Image by Chantel Concei for Sunday Times Australia)

Much like the Commute Crush, the Gym Crush is just as prevalent. Almost everyone I know has one and the same method should apply as with above – build up slowly. Also, word to the wise: don’t ask her out the moment she leaves her 55-minute Monday morning spin class – no woman want’s to be asked out when covered in that amount of their own sweat and tears. Get her when she’s fresh-faced post changing room or, even better, on her way into the gym. Nothing gives a work-out that extra kick than the confidence boost of a morning chat up.


Bar - TGJ

(Image: Louise Grinberg by Vincent Peters)

Girls tend to drink in packs and as intimidating as they make look, and contrary to popular belief, they are not all there for just a girlie catch-up over Cosmos. Every single girl in said pack is actually desperately hoping that one day someone like you might just cooly approach the group, single her out and ask to buy her a drink. Be that guy. You’ll be applauded for your confidence. If she says no, don’t be embarrassed, don’t let it knock your confidence – just remember that she will have been flattered regardless and maybe the next time you try it, it will work out.


Office - TGJ

(Image: Amanda Wellsh by Zee Nunes for Vogue Brazil March 2015)

Assuming you work in an office where inter-colleague relations are allowed and equally one big enough that any post-date awkwardness can be avoided by working on different floors and within different sectors, the workplace can be the perfect place to meet people. From a water cooler conversation to a flirt in the lift, the opportunities are endless and actually a whole lot less awkward than most other places on this list. Start by asking her if she wants to grab lunch on Friday together – see how it goes and then progress to drinks after work one Thursday. Easy.


on the street - tgj

(Image: Pattie Boyd and Tom Courtney, in the London rain, 1963, by John Cowan)

Probably the hardest of all the chat ups, the street is where it gets pretty tricky and you need an ample dose of confidence to be able to pull this one off. Essentially what you’re going to have to do here is physically stop a walking woman in her tracks to ask her for her number. No easy task my friends, but if pulled off, it’s basically the holy grail of smoothness. I will, I’m sure, be castigated for saying this, but I’ve asked many female friends, and after hot debates we think we may have come up with the perfect scenario for how we would like this to be executed were it to happen to us. Here goes:

Scenario: It’s your lunch break and you’re striding towards Itsu to grab your Chicken Teriyaki noodles, and then all of a sudden a vision comes striding towards you and all thoughts of Japanese condiments are swept from your mind. You both look at each other, a smile exchanged. “My god” you think to yourself, “what I would give to take that women out for dinner one night.” Well gents, now’s your chance.

Execution: Repeat in your head 3 times: “No woman is ever not flattered by being asked out.” Then turn on your heels, catch up with her, and stop her with a light touch on the arm and a charming “excuse me”, followed by, “I would never normally do this, but I just wanted to tell you how beautiful you are and I would love to take you out to dinner next week, can I take your number?” Done. Dusted. Pat yourself on the back, you’ve got yourself a date. If she says no? Who cares – you’re about to get a side portion of edamame beans with those noodles and no one needs to be any the wiser to your lunchtime antics.



Holly Macnaghten is the Fashion Director at The Gentleman's Journal

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