Dating Tips I Wish I’d Known In My Thirties

Despite being surrounded by friends with idyllic lives filled with husbands, babies, houses, engagements and near-approaching weddings, I am 33 and the Bridget Jones of my friendship group. Between heartbreak in my twenties and a laser focus on my career, I just haven’t been looking for love, and it hasn’t been looking for me either. 

Just before Christmas, on the train home, I found myself at the centre of a chance encounter like something from Richard Curtis film. A group of passengers sat chatting amongst themselves and a man across from me struck up a conversation. He asked for my number, insisting that he would love to see me again. 

Much to my surprise, I was quite ready to take him up on it. I had avoided dating apps like the plague because I just didn’t think they were for me, but here was a man in real life asking for my number. He may not have fit the mould of my fantasy husband, but when the opportunity landed in my lap I thought I may as well go out with him. 

Well, four weeks later and despite his many promises of an actual night out together, all I’ve gained is a list of excuses and cancellations, rather than a suitor. Despite the anti-climax of this short-lived affair, it did give me the courage to finally go on a date. “What could be the harm in downloading Hinge?” I asked myself. Little did I know I was about navigate a sea of mixed messages, rejections, and philosophical realisations. 

So, if you’re in a similar situation to me, here’s what I’ve learned re-entering the dating world as a 33-year-old woman:

1. You still can’t put all of your eggs in one basket

One of my oldest friends gave me an unsolicited monologue over dinner upon learning of my meet cute with aforementioned ‘train man’. “Rose, you’re not even that bothered about him (I wasn’t) and yet you’ll be livid when he lets you down. They cancel, they ghost you, you’ll be texting thick and fast and never hear from them again. But it’s normal. It happens to everyone.” 

At the time I thought this was terribly pessimistic. This guy had texted me every single day and even called me a few times ahead of our big date. However, when he fell off the radar without so much as a drink, I realised my friend was right. Just because we are older, doesn’t necessarily mean that prospective partners still won’t mess us around. Keep your options open. 

2. Beware of the PenPals

I always figured that if I ever downloaded one of the dating apps, I’d be out and about meeting my matches like Carrie in Sex and the City. Wow, I was wrong. 

My biggest revelation has been that there are so many people who will chat away with no real intention to meet. One guy I really liked the sound of, sent me big, long funny messages and asked great questions. After a week of messaging, I asked if he wanted to meet up, because quite frankly I didn’t want this to go on for a month only to discover we had no IRL spark. He shared his number and I thought this was going to be when we set a date, only for the big, long chats to continue. While I admired his willingness to get to know me, I’d be firm with these PenPals because there’s probably a reason why they’re stalling. 

Leave a Reply

Your email address will not be published. Required fields are marked *