I’m asking women to go for a coffee a week for a year — and this is how I’m doing it

This is the second in a series of articles I’m writing about going for a coffee a week for a year. The first one is here, and I recommend you read it to get what the hell I’m on about.

Today I had my very best day of “Coffee A Week” yet. I went on two. They both left me buzzing, both in different ways.

Going for a coffee a week for a year with an inspiring or simply super cool woman has been more of an incredible experience than I could have ever expected it to be — and I’m only about 8 weeks in. In that time, I’ve been for 13 coffees with 12 women and 1 man (you will note that I’m averaging more than one coffee per week — boom). If you want a little snapshot of what they looked like, who they were with and one lesson learnt from each, I’m collecting them here on Twitter.

It strikes me though, that while people are really excited and seem to… admire this endeavour of mine, when I suggest that they can give it a go themselves, such a suggestion is almost always met with apprehension. Simply because people don’t want to ask. From what I can gather, either they fear that it’ll put the other person in an awkward position if they don’t want to go for a coffee, or they fear that they’ll feel the rejection too much when someone says no — which, I have to say, does happen. Of course it does.

I have had a few “nos”. They fall into two camps. The first — and least common — being the “sorry I’m too busy, but good luck”. The second being that modern phenomenon of flat out blanking, particularly easy since we communicate with strangers from behind screens. I choose the former, a polite no thanks, over the latter any day, and have had lovely “thanks but no thanks” from women I respect and that have fantastic reputations. With good reason, I now see. The thing is, the first “sorry, I just can’t” takes the sting out of the rest of them. Even the first one doesn’t hurt that much because, at the end of the day, I’m just a girl, sitting before her computer screen, tweeting another girl, asking her to… go for coffee with me. I’m a no one and she won’t give two hoots if I’ve approached her with a proposition that doesn’t appeal to her right now.

“I’m just a girl, sitting before her computer screen, tweeting another girl, asking her to… go for coffee with me”

That’s what I really want to cover here though — the approach. So those who feel intrigued, but perhaps slightly intimidated, by this venture can consider how they could go about this. Maintaining our integrity and living according to our values is of paramount importance in all we do, and there’ll definitely be a way you can solicit the coffee company of women you admire without compromising on either of those things.

So here are three tips for how to do so. They’re just my suggestions and I would love it if you disagreed with all or some of them and came up with your own.

1. Choose your women wisely

There are women in my life that I fan-girl but know that I am not on their radar. One of them would be Bridget Christie, feminist comedian. Yes, we had a conversation once, but no, she will not remember who I am. But my god I love that woman. That said, I shan’t be asking her for a coffee any time soon. It’ll only make me sad that she’ll never be my wife if we do go for coffee anyway.

I don’t have a criteria for the women I ask for coffee other than they need to spark some kind of palpable interest in me (nor be potential wife material, with not a chance in hell). That’s it. There’s nothing strategic about it. That’s not what these coffees are for; they’re not for creating connections which I think will be useful for my professional career. At least, not obviously so. They’re for meeting women who make my eyes light up a little more and my brain buzz at a slightly higher frequency.

It might be a woman on twitter with a cool bio, it might be a woman I meet at an event who I exchange a few sentences with and I feel something exciting between us, it might be someone in my network already that I haven’t seen in years (today my coffee date and I worked out it had been about four years, after initially guessing two years). In fact, this little project can be a good excuse to ask that person you went for coffee with once but have always felt you didn’t have a reason to ask her again if they would like to do it again.

My advice would be to not be too narrow-sighted or prescriptive in what you’re looking for. I was at a fashion event last night and “fashion”, that’s fashion-fashion-darling, never is and never will be something that I have an involvement with beyond wishing I could shop at COS. But there were women there who I would love to go for a coffee with because they were forthright and ballsy and made me swoon a little. All that needs to be there is interest — if not in their industry, then in something they say or the way they do things. And I hope that it’s mutual; if not before the coffee, then definitely by the end of it.

2. Choose your channels wisely

This is about knowing your target audience but also about knowing yourself. I know, for example, that I am 100% more comfortable asking anything from anyone via written text. Meanwhile, for someone else, the idea of sliding into someone’s DMs with any kind of request at all is absolutely abhorrent. Personally, I feel I am able to better express my thoughts and desires in writing, while I have hugely charismatic, intelligent friends who are reduced to the least interesting people in the world when on messenger — except they’re not, they just find it impossible to type a string of more than three words and refuse to use punctuation or capital letters on WhatsApp. If you’re happier asking someone for a coffee face to face, then pick your moments when at industry events. I really enjoy getting a sense of someone in person and then saying “I’d love to spend more time chatting, shall we get a coffee?”. It just makes me more nervous, when I have no reason to feel that way.

I’m a fan of a private message on any of the social media platforms. That said, if I see that the woman in question hasn’t tweeted since October ’17, or has just 50 followers, I’m unlikely to use that as my channel of choice. Think how you think they’d like to hear from you, then go with that if it’s something you’re comfortable with. Smoke signals are fine if it gets you sitting opposite them with some beautiful latte art between the two of you.

3. Choose your words wisely

Don’t get me wrong, I believe in authenticity (gosh I sound like a wanker). I think we should know our own minds and then tell others what it is on our minds. I won’t make up any bullshit about why I want to go for a coffee with someone. That said, being an articulate young woman (I hope you’ll agree), there are any number of things I could say and ways I could say it, all with the aim of securing coffee time with someone cool. How do I pick my words? I think about what the other person is likely to respond best to. We all do it to some extent every day anyway, so it comes fairly naturally. It’s not hard to do.

For example, there are people who will respond hugely positively to “hey, I think you’re awesome and I would love to go for a coffee with you and hear your story”. They love the directness, that the message doesn’t take long to read; they don’t need an explanation or to be persuaded, and they love that you’ve popped up out of the blue.

Then there are those who probably want a little more of an explanation. Either as to what going for a coffee with you might be in it for them or what you’re after. Not in a selfish, cynical way, but because a lot of these fabulous women are time-poor and so they may want to understand what you have in common, or what you’re hoping to learn from them or talk about. Sometimes you have to know that people’s time is damn hard to secure and if you want to get some of that sweet, sweet time, you’re gonna have to do a little bit of pitching, using your fabulous personality and witty way with words as the hook.

I’ve found the first blog post I wrote on this project really useful as I can use that to explain why I’m asking them for a slot in their diary, seemingly out of nowhere. Again, you have to judge whether or not they’re going to take favourably to this. Some people will love the idea and they find it flattering, but I fear that others may see it as a strange experiment you’re involving them in to make up the numbers (not often though). It’s about knowing your audience and trusting your instinct.

Pearls of wisdom: done.

What I do want to really emphasise here, though, is that this shouldn’t feel like some over-thought process, governed by a set of rules about who you can and can’t ask for coffee and what you can and can’t say. I put these pointers together to try and elucidate how the process has been for me so far. I came up with them by reflecting on my experience thus far for this blog post specifically.

I don’t like rules or guidelines and having them would completely take the fun out of this for me. What I’ve enjoyed most is feeling a desire to ask someone for coffee and doing it. And not caring whether they say yes or no, other than it being a shame that I won’t get to meet that person if they don’t wish to. And then being completely surprised by the magic that can come out of nowhere when you meet that person with whom there is a little bit of electricity. Today was one of those days for me and I feel lucky, thankful and proud of my little project.

I’m going to write another blog post soon on what the point of all this is. What could I possibly be gaining from it? What I will say for now is I had the best day I’ve had in ages today, and it was because I had two “Coffees A Week” today — and one of them turned into two and a half hours and a delicious lunch with wine. Who needs a better reason than that.

Go on, be brave. Let me know if you’re going to do it and keep me posted on how it goes.