Fifty First Dates

Between the months of February to April this year, I dated a lot. It was sometimes bad, sometimes fun, but mostly just quite exhausting. You may know what I’m talking about. Your bank account takes a hit and you find you have to drag yourself out on a Monday evening when all you really want to do is curl up on the sofa eating cinnamon bagels for dinner. You also drink approximately three times the amount of your usual alcohol consumption during a week and wake up each morning with a moderate hangover, only to do it all again that very evening. And you haven’t even hit mid-week yet.

March 2019. By some weird, awful twist of circumstances I had a first date lined up for every day of a working week. It had been exhausting enough doing the admin behind each of those first dates. You’d think messaging five guys simultaneously would be fun and flattering, right? WRONG! You have the same conversation about where you live, what you do for a living and how many siblings you have…five, bloody times. Not to mention having to constantly re-read through each WhatsApp chat to check what you’ve actually said to each guy. My initial thought process stemmed from not wanting to put all my eggs in one basket. Never did I dream that all five dates would come to fruition, especially not all in the same week! London men were like London buses; there would be none at all and then they’d all come at fucking once.

My mammoth date week started on a Sunday. I had matched on Hinge with a guy from Hampstead who insisted on sending me voice notes at 5.30am every morning on his way to the gym. I hate voice notes. He suggested going out for a roast dinner at a pub in King’s Cross. I wouldn’t recommend going for a full-on meal on a first date. It’s difficult to answer questions with a mouth full of cauliflower cheese, and the weird cog motion you do with your hand whilst you franticly chew is just plain awkward. The conversation was mediocre at best until it took an unexpected turn and we ended up talking about male suicide rates for 20 minutes. Not quite first date material. After exactly two hours we politely said our goodbyes and departed at King’s Cross never to contact each other again.

The next day I woke up and couldn’t think of anything I’d like to do less than go on another date, especially on a Monday. Nonetheless, I headed to the Four Thieves in Clapham after work to meet the Australian bloke I had been texting. He was attractive but I wasn’t sure if there was a spark. After a couple drinks and some pleasant enough conversation I kissed him on the cheek and said goodbye. I noted that he chose to take the quickest route home rather than walk me to the bus stop. 

On Tuesday, the guy I had been messaging from Essex cancelled last minute. Halle-fucking-lujah!

Wednesday’s date was with a guy who worked in finance at Canary Wharf but also did some modelling on the side. He was clearly gorgeous in all his photos, but his texting chat had been quite dry. I presumed he was a model with no personality that had just sailed through life on his good looks alone. How very wrong I was. I turned up at Powderkeg in Battersea to be greeted by a very beautiful man. Before long I realised that he was also extremely charming and charismatic. I spent three hours drinking, laughing and resisting the urge to pounce on him from across the table. Apparently, that’s not socially acceptable. At the end of the date he ordered an Uber and insisted on dropping me off at my flat on his way home. Before I could even get my seatbelt on, hot model guy had slid across the backseats and cupped my face with his hand, leaning in to kiss me. Oh wow. We snogged all the way back to outside my flat, where I toppled out of the taxi giddy on wine and lust. Once inside, I text, thanking him for a lovely evening, and saying we should do it again soon.

I woke up on the Thursday morning in good spirits despite feeling hungover. I’d had a great date the night before and I was looking forward to my next first date that evening. I had been messaging Alan the most out of all five men. We’d been exchanging messages for a good three weeks and by text he seemed confident, funny and interesting. Alan had booked a table at bar by Clapham Common station and was already there waiting for me. As soon as I walked through the entrance and Alan stood up to greet me, my stomach dropped. 

The dangers of online dating include building up a persona of someone based on Instagram photos and text messages which could wildly differ from the actual real-life person. Before I’d even sat down at the table, I knew Alan wasn’t the person I’d built him up to be in my head. It wasn’t his fault, but I felt drowned by disappointment. And, being typically British, I knew I’d have to stay for at least two hours so as not to appear rude, or at least until we’d finished the bottle of wine he’d already ordered. 

“How was your day?” asked Alan.

“It was OK, how was yours?” I replied.

“It was good! How was yours?

“Um…we already did me,” I said.

Alan giggled apologetically; he was clearly nervous. After half an hour of chatting, my made-up persona of Alan was shattered. He wasn’t anything like the way he came across by text; I didn’t fancy him in the slightest. Plus, he had small hands! I’m sorry but I can’t get on board with small hands on a man. I have this theory; the hand/penis theory. The saying goes, ‘the bigger the feet, the bigger the…’ but bollocks to that. From my experience there has not been enough evidence to support the theory that there is any significant ratio between foot size and penis size. However, I have found that hands do! Not just the size, but also the shape and length of the fingers. If a man has chubby fingers that taper in at the end, then I bet my bottom dollar their penis is also chubbier at the base then tapers in at the top. Long, lanky thin fingers? Then long, lanky dick! Go on, test my theory.

Anyway, I digress, back to Alan. 9.30pm hit and I was desperately looking for an excuse to end the date. I checked my phone for the umpteenth time and saw a message from hot model guy. “Hey, I had fun last night but I don’t feel like we clicked. Have a good rest of the week.” I instantly felt my face drop. Alan must have seen it too. We didn’t click?! Mate, you practically pounced on me in the taxi! How much ‘clicking’ was needed?! Disappointment and frustration washed over me; any obligation I felt to stay any longer evaporated, I just wanted to go home. I told Alan I was tired and that we should call it a night. After the bill was paid, I got up from my seat and headed towards the exit. Alan quickly leapt up to follow me and started massaging my shoulders from behind. Oh God…the hands! I thought, repressing a shudder. Once outside Alan insisted that I catch a lift back home in his Uber. It made sense as his station was on the way to mine. I couldn’t think of a reason to decline… fuck sake. 

As we waited outside for the Uber to arrive, I must have been shivering because before I knew it Alan had wrapped his scarf around my shoulders. “Oh, thanks,” I said, giving him a half smile. Next thing I knew, Alan had enveloped me from behind in a tight hug and started swaying me from side to side. I froze. Dear God…make it stop! Againbeing too British to say anything, I awkwardly stood on the pavement, my arms dropped by my side, whilst Alan, completely unaware of my inner turmoil, continued to rock me like a baby. When the taxi eventually pulled up, I practically threw his arms off me and bolted inside. I placed the scarf on the middle seat to act as a barrier between us (there would be absolutely no sliding across the backseats on this date!). 

As soon as I closed the front door behind me, I got out my phone and texted hot model guy saying, “no problem”. At least he hadn’t ghosted me. I then constructed a message to Alan. I thanked him for the evening but explained that there was no spark for me. Sent. I breathed a sigh of relief. What a week. It felt like I had gone full circle; all that energy, money and the hangovers and I was right back to where I started. This dating malarkey was draining.

I decided to give Monday’s guy a second chance; he was attractive and seemed nice after all, maybe I was just tired at the time. We saw each other a couple more times, and by our third (and what would be our last date) he invited me round to his to ‘Netflix and Chill.’ However, this was taken in the literal sense. We laid on his bed fully clothed and watched an entire film, only pausing when I noticed that he’d fallen asleep…again. This was a third date; surely, we should be overcome with lust, ripping each other’s clothes off?! The film finished and I made a comment about heading off home soon. He nodded and gave me hug. A minute later and he started to kiss me, but I just felt like we were going through the motions. I opened my eyes and looked down to see one of his hands awkwardly squeezing my boob over my top. I felt like a human stress ball. Just close your eyes, Jess. He then decided to weave his hand down the collar of my top to grope my breasts; his elbow sticking out awkwardly in my face as he dry humped me over my jeans. This was the least sexy thing ever. After 15 minutes of this I gave up, thanked him for a nice evening and made my way home. He didn’t walk me to the bus stop. Again.

Come April I decided to take it easy and just date one guy at a time. I had matched with Malcolm, a lawyer who worked in the West End. Malcom was tall and kind of goofy but in a cute way and we immediately hit it off. For our second date we met in a bar off Oxford Street where in true classic Jess style I managed to lock myself in a toilet cubicle. After a panicked 15 minutes calling out to random women in the bathroom, I was eventually rescued by the bar staff. “I thought you’d had an accident or something…” said Malcolm, as I re-joined him, ever so slightly flustered. We then headed around the corner to Swingers crazy golf.

We had a fun evening; drinking and kissing in between playing the holes. As our timed golf session came to an end, Malcolm suggested going back to his. I quickly weighed up my options in my head. I didn’t want to sleep with Malcolm that night as I already knew he was off in a few days’ time for a solo holiday to Brazil. No way was I about to have sex with a guy before he went gallivanting off for three weeks; I did not need that kind of anxiety! But I also didn’t want the date to end, so I agreed to go back to Malcolm’s to hang out. That night, we stayed up to 4am chatting; we were completely naked in bed the whole time, but I was adamant that we weren’t going to have sex. And we didn’t. We eventually fell asleep spooning. The next morning Malcolm was very sweet, he let me use his toothbrush, ordered me an uber home and gave me a banana on my way out (not a sexual pun). He kissed me goodbye and said he’d see me when he was back from Brazil. That was the last time I saw Malcolm.

We exchanged a few messages whilst he was away and although Malcolm was friendly enough, I found it was always me that was initiating the conversation. As the days in April rolled by, the messages became fewer and fewer whilst each new day (according to my Instagram feed) saw Malcolm follow approximately 50 different Brazilian girls. I couldn’t blame him; he was obviously enjoying his trip. A lot. But I didn’t want to be just an option in a pool of women he had matched with on dating apps, in the UK or otherwise. So, I decided to date other men and make Malcolm the option instead. 

Throughout my two months of intensive dating I didn’t allow myself to get too close to anyone. Most dates ended with a kiss on the cheek, a few with a snog and only a couple went beyond first base. “You can’t catch feelings from the finger,” as my flatmate, Jasmine  said. And it was true. I didn’t sleep with anyone in five months. By having sex with any of these men I would have allowed myself to be vulnerable and I just wasn’t prepared to do that. So, I kept any exploits strictly PG.

I have a love/hate relationship with dating apps. On the one hand, it’s amazing to have access to all these seemingly eligible men at the swipe of a finger. If you wanted a date or shag one evening you were only a few clicks away from obtaining it. Genius. On the other hand, as with everything where there is too much choice, people tend not to put very much effort into it. There are always other options, endless conquests to be made, plenty more fish in the sea… So, why bother sticking with the mackerel you went on three dates with when you could be simultaneously dating cute cuttlefish, gorgeous guppy and sexy sea bream. Even if you did quite like the mackerel in the first place! Ok, enough about fish.

Gone are the days of men trying to woo a woman with surprise picnics, flowers and turning up in convertible cars to declare their undying love (see, Richard Gear in Pretty Woman). Men no longer make the effort. They are too busy lining up their next conquest, and it’s all in plain sight on Instagram. Apparently, the grass seems greener on a new girl’s profile. Rolls eyes. I wanted a man who walked me to the bus stop, who messaged to check I got home OK, who didn’t follow the other hundred girls they had matched with on Hinge. I wanted someone to prove to me that romance was not dead. And none of these guys I dated could.

The reality is that none of these men were right for me and I wasn’t willing to settle. Not anymore. I wanted someone who added to my life, supported me and would do the little things just to make me smile, because they wanted to and not because I asked them to. Someone who could make me feel wanted, secure and special whilst also setting my heart racing. I wanted a man with big hands! So, after a couple of months of dating, I made my peace that it would probably be a while until I met someone that could match up to that and that I may as well enjoy the upcoming summer being single. And then, as the cliché goes, when I was finally content in my own skin, when I least expected it… I met someone.

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