Life Relationships Five dates in five weeks: one woman’s diary

Five dates in five weeks: one woman’s diary

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So, confession time: I can’t run. At all. Whilst I have the technical apparatus to complete the task (legs, knees, cute sneakers), my joints are toast. So while the lycra-clad masses run endless marathons, us mere mortals need to be a bit more creative when it comes to fundraising.

By dating. No, really!

• A tinder user’s first time
Digital dating and the sly art of the ‘vanishing act’

I first heard about Five in Five last year when a former housemate (wo)manned up and smashed out five dates with five total strangers like a boss. She suggested that I should do it too, however my response at the time was essentially a grumpy cat face.

“Do I look like I know five single guys??? How would I even find people? Smoke signals? Ouija board? Giant sign around my neck?”

However, when you take the potential rejection out of it – it’s for charity so you both have to say yes – suddenly your options increase exponentially. And at the end of the day it’s just coffee and a chat, no sonnets or proposals required. What’s so hard about that?

Asking someone out

Within the first 24 hours of Five in Five, I learnt something unexpected: I can’t ask someone out.

There I was, looking dateable, when a cute bearded man appeared. He gave me his business card and I promptly palmed him one of mine before we skipped into the sunset to have adorable bespectacled offspring.

Er, not quite.

In reality when I opened my mouth to lock in my first of five … nothing came out.

As such, Five in Five became a personal challenge: Feel the terror and do it anyway.

I emailed him and he said he would love to. Thank god for that.

Date one

Date #1 was with Cute Bearded Guy, in the city, for coffee. I had chosen the venue based purely upon Urbanspoon ratings, so I was understandably worried. I went for coffee as the most casual, least heart attack inducing option, but what if he’s a coffee snob? What if he turns out to be some other kind of weirdo? Worse, what if it turns out *I’m* the weirdo?

He wasn’t. He was actually exceptionally lovely, despite being born in a different decade (Whoops. Beards are clearly misleading).

We chatted easily but at the end of the day, it wasn’t to be romantically speaking. It happens. I don’t regret asking him out, because I proved to myself that I can do this. The actual date part was just gravy.

Date two

After a surprisingly easy Date #1, I was a little less apprehensive for Date #2, despite the fact it was a blind date. I knew nothing about this person other than his name and phone number, but he got points for using full words and actual grammar in his messages.

Expecting the worst, imagine my shock when he turned out to be not only cute and nice, but also interesting. In my life that trifecta is like Halley’s comet, only less frequent!

In fact I liked him so much that not only did our half hour charity coffee turn into a 2 hour gab-a-thon but I happily arranged to go out with him again.

Erin West embarked on a dating journey with four different men.
Erin West embarked on a dating journey with four different men.

Date three

So Date #3 was actually with Guy #2 and I had a fabulous time…but a lady never tells, so onto Date #4!

Date four

This was with a friend of a friend who actually took the lead and organized the day, time, and venue. He was also a total sweetie and most impressively paid for everything to allow me to donate the money to charity.

Date five

Date #5 ended up being the best of all. He not only put up with my scheduling conflicts (third attempt was the charm), but also insisted on paying and offered to pick me up. For a charity date, that is definitely above and beyond.

Over all the guy gives good date and he was dressed to impress, which made me feel virtuous for bothering to wear makeup. We are now Facebook friends and I think I may have a potential recruit for Five in Five next year.


Perhaps it is the horror that I have previously endured at the hands of ‘love’ (ever the fickle mistress), but I went into this Five in Five thing totally petrified. Turns out, it’s actually easy, and most importantly, FUN. Who knew?

Let that be a lesson to us all. If, like me, you despise online dating, do not despair! You too can meet several ridiculously lovely young wo/men in real life. You just need to be brave. It’s doable. Trust me.

Five in Five is a campaign which encourages single people to pledge to go on five dates in five weeks, raising money for the urban poor in our community.

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