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5 things I wish I knew before navigating online dating at 33

5 things I wish I knew before navigating online dating at 33

If Bridget Jones joined Hinge and found everything but love.

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.

Having lost all patience altogether, I forgot about him for a moment and tried a new tactic. This formed the basis of my next revelation.

3. You’re wasting your time worrying about yourself – be more worried about whether they are right for you

Among the talkers, there was one guy that had suggested we meet for a drink very early on. Stephen* made a bit of a weird joke when I said that I worked for myself, suggesting that I obviously binge watch reality TV all day. This was either a funny comeback or he was my biggest pet peeve of all time – a know it all. Throwing caution to the wind I agreed to meet him, only for him to talk about himself the entire evening. On reflection, I couldn’t believe the amount of time I have historically spent worrying about how I look, only to find myself sat across from someone this self-important and boring. Instead of worrying whether you are good enough for him, get really clear about what is good enough for you! Bad manners are a total no-go for me, in any event.

4. Honest communication reaps good karma

After the world’s most boring evening of Stephen talking and me listening, I was surprised to receive an invite to a second date. Despite him not stopping for air all evening, I didn’t want to be hurtful. I explained that though it was lovely to meet him I just didn’t feel a connection. He replied and thanked me for my honest approach, and I attracted the same karma to myself the very next day. If you’ve been caught out by mixed messages in the past, show your date the same courtesy you’d want to receive and be clear and kind in your communication.

5. In spite of all of this, you may have your faith restored in humanity…

Re-evaluating my many stop-starts, I decided to come out and ask Jason* from Hinge (the texter) on a date. No big long texts, no ‘how was your day’, I sent a simple “do you want to go for a drink this week?” with the hope of a succinct yes or no. Though his answer was no, he has kind of restored my faith in humanity. “I’d love to go for a drink, you seem like such a great girl, but I’ve just started seeing someone and I think it might go somewhere. I doubt you’ll be single for long – you’re a catch.” Whether we believe him or not, it struck me as especially kind to give such a soft blow to someone you have literally known for two weeks. So, no, I haven’t found a gentleman on Hinge just yet, but his rejection has given me hope that I still might.

Among all of this chaos of dating again in my 30’s there is one undeniable pull – I’m having such a laugh debriefing all of this with my friends. If you happen to be reading this and you’re the Bridget Jones of your friends, give it a try, put yourself out there. You might not find someone right away, but, believe me, your friends are going to count down to your voice notes while you’re looking.

If you need me, I’m going speed dating next week. God help us all.

*All names are changed.