I’m 41, and (unhappily) single – which has been a theme for the majority of my adult life. I was 27 the last time I was in a committed relationship. We were both very career-focused and at first I didn’t mind that he didn’t really want to settle down, but then I realised it was never going to “go somewhere”. Dating after that was a minefield. There were the men who lied about what they were looking for to try to get you into bed, the Peter Pan boys who never wanted to grow up, the love-bombing narcissists and the ghosters to name a few. After an on-and-off five-year situationship (that started with him having a girlfriend that I knew nothing about) came to an end, I felt completely defeated. At 37, my self-esteem was at an all-time low. I had become super distrustful of men, and it felt like all the good guys were taken.

Pausing and reconnecting with myself

Looking back now, it probably made little sense to take a three-year dating break so late in my thirties, given that what I’ve always wanted was to fall in love, get married, start a family and live happily ever after. But I deleted the apps and decided I wasn’t going to date. The timing wasn’t ideal and I felt stressed that my biological clock was ticking. But I needed to pause and reconnect with myself. I froze my eggs, went to therapy, and had somewhat of an outward makeover (think some weight loss, Invisalign, and a hair transplant). So, while I have felt pretty lonely at times, I have also felt a lot stronger emotionally and better about myself inside and out. Seven months ago, I decided I was ready to get back out there. However, during my time of introspection I realised a few things: I wasn’t good at enforcing boundaries, was perhaps a little too picky and I didn’t really know what I was doing when it came to finding lasting love. I tasked dating and compatibility coach Caitlin Smith (pictured) with helping me figure it all out over two weeks and three sessions. View the following slides to see what I learnt.

Date with intention, not on autopilot

Despite the fact that I thought I knew what I wanted I very quickly fell into accepting dates from men simply because I thought they were attractive (or they asked me out). Smith urged me to clarify what kind of partner I wanted. “Figure out who aligns with your vision, what your deal breakers are, and how you want to feel in a relationship.” I decided I wanted to be with someone who was kind, funny, empathetic, a good communicator and who I was politically aligned with. I didn’t want to date anyone with children, but they needed to be open to having them, and equally fine with not. Smoking and vaping is a no-no and a somewhat stable profession (since mine as a beauty and lifestyle editor is anything but) is a must. Drilling down on my requirements made my swiping on apps more targeted and my conversations in person more focused on figuring out if my dates would make a good partner for me. (Photo: Beata Zawrzel/NurPhoto via Getty)

Imagine life without motherhood

I’ve always wanted to be a mum, and over the last seven months while I’ve been back on the dating scene, I’ve found I’ve started to feel sad and anxious about how time is running out for me. “Our biological clocks are one of the biggest internal pressures for women, especially when meeting someone is tied up with starting a family,” says Smith. She advised me to get clear on my stance around motherhood. “Try to imagine a Plan B – what would your life look like if you had children by yourself, or didn’t have any at all. When you get more comfortable with that, you stop dating with a sense of panic – which is where things can often go wrong,” says Smith. I’d already decided mainly due to finances that solo motherhood wasn’t for me – but I hadn’t envisaged with much positivity what my Plan B life would look like. I started visualising a full life without my own children. One, where much like now, I got to spend lots of quality time with my niece and nephews. A life where I had lots of flexibility and could do anything I liked at a moment’s notice. I also started to appreciate how my time and money were my own, that I could sleep in whenever I fancied and I was free of the stresses raising children held. This Plan B life could also involve a partner but said partner didn’t have to materialise before a certain time, and that helped quell that sense of urgency that had started to creep back in. (Photo: AlexLinch/Getty/iStockphoto)

Swipe like a friend is setting you up

I complained about the fact that I rarely swipe right on dating apps, mainly for superficial reasons: far from perfect teeth, receding hairline, “basic” dress sense, etc. Smith urged me to “stop looking for reasons to say no, and ask: If my best friend said this person was funny and great, would I say yes?” This one really resonated with me. Would I be so put off by a man’s “basic” dress sense if a friend vouched for him? Maybe not. “We judge far too harshly on apps. Remember, there’s a real person behind the profile, and if you met them in a bar and you clicked, you wouldn’t be overly concerned with what style of shoes they were wearing,” says Smith. I kept Smith’s words in mind when swiping and as a result I got a lot more matches. In theory more matches should result in more dates, which relationship psychologist Julie Schwartz Gottman tells me is what I should be aiming for, as we should all be “dating as many people as possible, to discover what you really want in a person”. (Photo: Tim Robberts/Getty)

Get comfortable with yourself

“Being yourself is important when it comes to building momentum when dating. Often women who have been told they’re ‘too much’ in the past try to be cookie cutter, passive and nice – but what comes across is someone who lacks personality and isn’t genuine. Don’t be afraid to be yourself,” urged Smith. I needed to hear this. As someone who has never felt good enough – which stems from a myriad of things such as the competitive nature of the private schools I went to, the value my grandma held on appearance and the fact that I was often the only person of colour in the spaces I entered – I have always found it incredibly difficult not to over-analyse how I come across on dates. The culmination of these experiences resulted in a sense of low self-worth that often saw me entertain the advances of men who ultimately didn’t respect me. Needless to say, being given the permission to just be me – especially when many dating gurus promote game playing and strategy over being genuine – felt revolutionary. (Photo: Anastasiia Krivenok/Getty)

The three-date rule

For many of us (including myself), consistency can feel boring. “When you find yourself in a grey area where you’re no longer attracted to people who are unavailable but you’re also not particularly attracted to people who are – then you need to go on at least three dates with a person, before cutting them loose,” believes Smith. I liked this idea because I had found that I’m very quick to cut and run if I don’t “feel” anything. Smith shared that this three-date rule would help retrain my brain, allow me to get to know my dates better and help me make a more informed decision when it comes to deciding if I wanted to take things further. I’m up for putting this to the test the next time I get asked out. (Photo: d3sign/Getty)

The result

It’s still early days, but I’m feeling positive, and energised and unlike before I actually believe that I might still meet someone and fall in love – because I know what I want, what’s important to me and that who I am is enough – and maybe that’s half the battle won.