Making the first move: Meet four women who took the initiative and pursued their partners

Posted by
Harriet Hall
backgroundLayer 1
Add this article to your list of favourites

Modern dating is a tricky thing. Sure, we've been given a helping hand thanks to dating apps such as Tinder and Happn, which help strip-away any awkward 'friend-zone' predicaments and the do-they-don't-they-fancy-me vicious cycle. It helps to know that you are both in contact because you fancy each other and want to see where it goes.

And yet, dating apps still haven't managed to solve the age-old question of who should make the first move. 

If we’re honest with ourselves, even in our emancipated, empowered fourth-wave age where we guffaw at the idea of a man paying for our dinner (please, we’ve got this…well, our half at least), many of us still hesitate to make the first move when it comes to dating. 

It’s not that we don’t feel that we should or that we don't want to come across too keen (because, really, we DGAF) but it still feels a little nerve-wracking. Perhaps two thousand years of patriarchy didn’t prepare us efficiently for the dating world, or perhaps we secretly want to know one hundred percent that the bloke fancies us as much as we fancy him.

With that in mind, we spoke to three women who threw caution to the wind and said ‘sod this, Ima bag my man’, making the first move in the beginning of their romantic journeys. We asked them what encouraged them to make the first move, if they felt nervous and how they prepared. Here’s what they had to say…

Stacey made a move on finance Sam after lunch one day at college

Stacey (25) is a graphic designer from Bradford. She made the first move with her partner, Sam (24) when they met seven years ago. They are getting married next year.

When we met: “We met through a mutual friend back when MSM and MySpace were the thing. I thought Sam was absolutely beautiful and we started chatting online nearly every day after college."

Why I made the first move: "He was really shy and had never been in a relationship before, so after a few months I took the wheel."

What I did: "I made a move after he walked me home one afternoon. It was raining, and when we hugged goodbye I looked up at him under his hood and kissed him and he kissed me back."

How I felt: "I felt really confident and pleased it had finally happened."

How he responded: "He kissed me back! I felt really confident and he was a little nervous, but we were both left buzzing that it had finally happened."

How long we’ve been together: "We’ve had a joined-at-the-hip relationship ever since. Last year, we were on holiday and he got down on one knee and proposed. The wedding is next year and we cannot wait.”

Jo propositioned Chris at a friend's wedding

Jo (34) is a project manager from London. She decided to initiate things with Chris (35) at her friends’ wedding three years ago. They were married in November last year.

When we met: "I met Chris in 2012 through a couple of friends and often bumped into him at events they were hosting. He was tall, funny and kind and we got on well."

Why I made the first move: "At my friend’s wedding, I realised it might be a while before I saw Chris again and I remember feeling quite sad about it, so I decided I would have to make a move."

Making the first move: "I’ve never made the first move before. I’ve always been horrendously shy I was horrified at the thought of him rejecting me but I was more concerned that I might not see him again."

What I did: "I built up courage by discussing my plan of action with a friend over several shots, then approached Chris and launched into a speech about how it was time we went on a date, just the two of us. Then I leaned in and kissed him."

How I felt: "I definitely don’t regret making the first move – I don’t think he was planning on it so I had to do something! I think Chris was surprised but I don’t think making the first move has anything to do with gender - it’s just a matter of confidence."

How he responded: "The next day, he texted me and asked me out."

How long we’ve been together: "A year and a half later, Chris proposed and we were married last November."

Tess passed Ben her number on the Tube

Tess Henderson (26) works in PR and lives in London. She met her partner, Ben Gardiner (25), a project and studio manager, on the Central line and passed him her number on a receipt.

When we met: "We met on the Central Line one Saturday afternoon a year and a half ago. We were making eye contact over our books."

Why I made the first move: "I knew once I got off the tube I would never see him again, so I had nothing to lose – even if he didn’t respond."

Making the first move: "I had never had such a strong feeling about someone that compelled me to do something like that before. Gone is the age of waiting for guys to make a move, go for it. You feel amazing afterwards because you have done something for you."

What I did: "I looked for a receipt to write my number on - first all I could find was a Tampax receipt! Eventually I found a suitable one and got ready to give it to him in a casual but sophisticated move as I got off the tube."

How I felt: "I was so nervous that as soon as the announcement came that the next stop was Oxford Circus, I got up, bright red, didn't say a word and thrust it in his face. Then had to stand by the door for about a minute (felt like a lifetime) when the tube rolled slowly into the station. I wanted the ground to swallow me up! When I off I was shaking from nerves."

How he responded: "He smiled and then tried not to look at me too much as I was so embarassed. That evening, he texted me and I was over the moon. Later, he said he was very pleasantly surprised and encouraged by my confidence."

How long we’ve been together: "18 months and counting, best relationship I have ever had and we are really happy."

Caroline proposed to boyfriend Philip

Caroline (30) is a project manager from South East London. She met her partner, Philip (34), on After being together for six years, Caroline popped the question to Phil. They have been married for a year. We asked her if she always made the first move…

Where we met: We met on

Why I made the first move: It wasn’t really the first move, but I proposed to Phil. I did it because it felt like the right time for us to get married. Plus, this way I wouldn’t be surprised…I am AWFUL at surprises.”

Making the first move: "I definitely don’t usually make the first move, but meeting online makes that all a little easier."

What I did: "I made him a sausage sandwich for breakfast and wrote “Will you marry me?! in ketchup on a salver I bought on eBay. My friend lent me an icing bag to use for the writing but it all got a bit messy. I had to point out the message as he almost missed it."

How I felt: "I was nervous but I was fairly sure of what his answer would be."

How he responded: "He followed his ‘yes’ with a slightly indignant “I was going to do this!”. I think he was a little taken aback. It wasn’t a leap year, I think that’s all a bit daft to be honest."

Images: Rex Features

Share this article


Harriet Hall

Harriet Hall is a former Stylist contributor.