I dated 50 men in three years and it broke me

Jennyfer Jay
28 min readJan 13, 2024

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When I became single at the end of 2020, I had no idea of the hell that was waiting.

I’d made the difficult decision to end a year-long relationship with a good guy (honest, loyal, thoughtful, and genuinely cared about me) because our values didn’t align (I won’t go into why), and deep down I knew we had no future.

I was sad about it, but happy to be single. And I was in a great place — a homeowner, I worked for Google, and had just lost two stone (30lbs) after years of hating my body. I was feeling myself, and certainly didn’t need a man.

Then, just three weeks after that break up, I met the first of the 50 guys I was to date over the coming three years, and found out dating post-pandemic was a shit show.

Men had gotten used to walks in the park and a Big Mac meal in McDonald’s car park being an acceptable first date (since that’s all you could do in lockdown). Love bombing was now standard practice. And commitment? Well that seemed to have been erased from people’s vocabularies and replaced with phrases like ‘figuring out my dating goals’ and ‘ENM’ (ethically non-monogamous).

The dating bar had plummeted to below sea level.

What follows, is a synopsis of each guy I dated, in chronological order.

When I say ‘dated’, I either FaceTimed them or went on an in-person date. The hundreds of men I chatted to on the dating apps, spent days voice noting, or even hours chatting to on the telephone, didn’t make the cut, since they could have been anyone.

50 first dates. Let’s do this…

#1 (we met IRL)

The worst guy I could have met when I’d just come out of a healthy relationship and my guard was down. We met through friends, and he was sold to me as a “hopeless romantic, ready to settle down”. Red flags should have been flagging when, the night of our first date (and second time meeting), he said, “I really like you”, and in some odd bid to prove he was serious about me: “I always tell girls I just want something casual but they fall in love with me anyway…” Sadly I was in my naive girl era and just brushed the comments off as odd.

What he was actually doing was love bombing me; phoning me for hours a night, talking holidays, babies, homes, and calling me “future wifey material”. He introduced me to his friends and told me he “really liked me” every single day for two to three months. So there was me thinking he actually liked me…

Except he didn’t. One day out of the blue, he went ice cold and said the mother of his child had hurt him so badly he wasn’t interested in being vulnerable again.

I ended things immediately.

He came back a week later asking for another chance, saying: “If I can’t make it work with you, I can’t make it work with anyone and I don’t want to end up a lonely old man…”

I’d started to really like the boy and actually saw a future with him, so it was everything I wanted to hear. I gave him another chance, and he lasted a whole week before turning to ice again.

Despite him also telling me some enormous lies, like he had 20K saved for a deposit on a house (he had no savings) and that I didn’t need to worry about his baby mum (he went back to her when we stopped speaking) I still couldn’t bring myself to cut him off.

His avoidant behaviour had triggered my anxious attachment, and was dredging up abandonment wounds from childhood — the only antidote to my rapidly-eroding self-esteem (due to him treating me like I was worthless) was his attention and validation.

I continued accepting his scraps for a few more months until he finally admitted he had never wanted a relationship with me, something he realised “pretty early on”. Well thanks for letting me know, pal.

I cut him off and told him never to speak to me again (go me!), but still thought about him every day. It was some real-life Allie and Noah shit (only on my part, of course).

Exactly one year later, on holiday and in a ‘yolo-y’ mood, I text him. He replied within seconds, and the can of worms ripped open with abandon. We were straight back to morning and good night texts and daily phone calls, like no time had passed. He even tried to rearrange his whole holiday when he found out we were going to the same destination, just a couple of weeks apart.

I knew I couldn’t trust him and he was never going to be my person, but he was gorgeous, super affectionate and amazing in bed, so I pretended I was happy with us just sleeping together.

Until I found a girl’s stuff in his bathroom when I was staying over one night. “I’ve only been seeing her a couple of weeks…” he said. “I’ve been planning on ending things with her because she’s too needy… she called me up when I was at the pub and asked me not to get with other girls.”

This poor girl, who clearly thought they were serious enough for her to leave her belongings at his house, was feeling insecure and asked him not to get with anyone, and there he was the very next day with me in his bed.

And that’s when I realised, after two years of wondering why I wasn’t good enough for him, this is just what he does: meets girls, love bombs them, makes them think he really likes them, and as soon as they like him back? Goes cold.

I lost respect for him as a person after that and tried to distance myself (albeit unsuccessfully) and he ended up cutting me off for unrelated-reasons not long after. I was completely heartbroken, but I guess he did me a favour.

#2 (Tinder)

This guy over-shared his family traumas on the first date (red flag) but was the perfect gentlemen — he was one of only two men I’ve met who practice the ‘pavement rule’. He ended up ghosting me after two dates (not quite so gentlemanly), which I wasn’t mad about as I wasn’t sure I fancied him anyway.

He popped back up three years later (they really do always come back) and his life was in chaos. His mum was recovering from cancer, his grandad dying of cancer, and his ex and his best friend had not long run off together. He also told me an insane story about how he’d had sex with his therapist, then she tried to blackmail him, and now a therapist she works with gives him free sessions to keep him quiet. I declined his offer to meet for coffee and he vanished again. He seemed liked a nice guy deep down, but clearly super troubled (like many men on the dating apps).

#3 (Tinder)

Number three was good looking, but our humour didn’t gel and it made our park walk date a little awkward. Another first date oversharer, he told me how he’d been hospitalised with alcoholism, and gave me a full rundown of all his sister’s issues too. He didn’t speak to me for a few days after the date, so when he asked for a second, I used that as my excuse to say no.

He popped up a year later and asked if I wanted to go out again. I told him I was no longer dating.

#4 (Tinder)

When we FaceTimed, this guy told me he has no friends and just spends time with whatever girl he’s dating at the time. He asked to go on a proper date and I told him he was too young for me. That felt more polite than saying, “No thanks, serial killer.”

#5 (Bumble)

I dated number five for three months and even went on holiday with him — I could tell he was a lovely person, just the type of guy I needed to be with after my ordeal with #1. But the attraction, nor the sexual connection was there, and he was depressed. He’d often make jokes about wanting to kill himself, which wasn’t helping my own mental health. He asked me to meet his friends and be his girlfriend multiple times, but it all felt wrong and I kept saying no.

As soon as we went on holiday I realised I didn’t want to be there with him. Or with him in general. My decision solidified further when we had an argument about the Sarah Everard case when it came on TV. He said the police were unfair to go down the group chat Wayne Couzens was in because men always write outrageous stuff in group chats, and that he (the guy I was dating) should feel more unsafe on the streets than me (a woman), because more men are murdered by men every year than women… yes, by other men.

I ended things soon as we got home and still feel bad for letting that go on longer than it should have.

#6 (met IRL)

This guy asked for my number at West Ham football stadium. We met up one Halloween (me dressed as a prisoner from Orange Is The New Black and him a robber from Money Heist) and I quickly realised he was a massive coke head — because he literally had coke visibly up his nostrils. After that he kept booty calling me at 2/3am every Friday so I blocked him.

I matched with him again on the apps two years later — he was still a coke head, and still only wanted sex.

#7 (Bumble)

This guy had great banter, a cute dog and went to my gym so of course I had to meet him. We had three really fun dates, then he literally sobbed on my shoulder about his ex and I realised he was a) not over her, and b) sleeping with multiple women. Neither of us wanted to pursue anything romantic, but since we got on so well we became friends.

#8 (Tinder)

Went on a fun axe-throwing date with this guy. I wasn’t sure I fancied him, he was a fair bit younger, and on the date told me he wasn’t looking for anything serious… so when he asked for a second date and tried kissing me, I declined on both counts.

#9 (Tinder)

FaceTime date with an Aussie guy. He was nice enough, but neither of us were feeling it and we didn’t speak again.

#10 (Bumble)

Another guy who seemed nice enough on our pub date (although a little distracted — he keep looking around the room the whole time, which I took offence to). Clearly neither of us were bothered as we didn’t go out again.

#11 (Bumble)

Probably the worst date I’ve ever been on. This guy wasn’t even my type, but he was acting super keen so I thought I’d give him a chance. For the date, he told me to meet him at the pub where he was watching football with his brother, then said we’d go for food.

Unfortunately for me, Arsenal were losing that day, so when I walked in he was in a foul mood, and barely looked up from his iPad to say “hello”. When his brother, who was courteous enough to make conversation with me, went to the bar to get me a drink, I turned to my date and said: “Shall I just go home?” He replied: “No, I’ll be okay once we go for food.”

As the football ended and we all got ready to go, the brother just stood there awkwardly. Because I’d spoken to the brother more than my actual date I said: “Why don’t you come for food?” He accepted and I went for Thai food with my date and his brother.

It transpired they were on the third day of a three-day sesh, which explained some things. The guy asked me to hang out after and offered for me to stay at his. “No thank you,” I said, and we never spoke again.

He messaged me a year later to say I looked hot in my Whatsapp photo and admitted “maybe bringing my brother on the date wasn’t the best idea…”

#12 (Thursday app)

FaceTimed this Ukranian guy and we got on really well and planned a date in. I ended up getting a migraine the night before and asked to rearrange. He got really moody and said he didn’t want to rearrange. So I said, “Cool, let’s leave it.” Later that night he came back and said, actually, he did want to go out still. Because he got so shitty with me, I declined.

#13 (Tinder)

Had a FaceTime call with this lawyer. He looked way worse than his photos which must have been Facetuned, and kept checking himself out in the camera, raising an eyebrow and pouting the whole conversation. After our call he kept trying to invite me to an exclusive sex party in London, which was the final nail in his pouty coffin.

#14 (Tinder)

Met this Croatian footballer in Ibiza. He was lovely and we had a great night out, apart from me being sick and him having to drop me home. He went to Valencia the next day so I never saw him again sadly.

#15 (met IRL)

Went to my friend’s wedding and hit it off with her brother and we spent most of the evening together. He wasn’t the one, though, due to being a lot younger than me and a complete fuckboi (he had a neck tattoo of the Devil whispering in his ear…)

#16 (Tinder)

Had two pretty nice dates with this half-Japenese guy. He was really boring over text so I wasn’t sure if there was enough of a connection, but I’d have been up for a third date to make sure. After being complimentary on our second date, telling me I look better in person than in my photos, and saying he always tells girls when he’s not interested rather than ghosting, he ghosted me.

We rematched on Bumble a year later, and despite saying he was excited to see me, he ghosted again. No big loss since his chat was dead.

#17 (Tinder)

FaceTimed this English-Mauritian guy — he told me he had a foot fetish and that he wanted to take me to get my nails done before our date. That put me off somewhat, so no tears were shed when I didn’t hear from him after the call.

#18 (Tinder)

Had an hour-long Facetime with this estate agent from London, was going well until I mentioned I’m vegan. “Oh I could never date a vegan!” he said. “If I’m going to eat three meals a day for the rest of my life with someone I don’t want any of them to be vegan.” And we ended the call almost immediately.

#19 (Tinder)

When I matched with this guy, his mum was devastatingly receiving end of life care for cancer. I was a little worried he was using me as a distraction when he started FaceTiming me multiple times a day.

We made a date and he (understandably) cancelled on me 20 minutes before. When he apologised a few days later and asked if we could get another date in the diary, I said it’s not a good time for him to be dating and we should just leave it. I was super bummed, as he was gorgeous, and I’d gotten used to talking to him every day, but I knew it was for the best.

A whole year passed, and he popped up on Hinge — we instantly matched and got chatting again. He seemed in a much better place and we had some really lovely dates together.

He was the first person I could see myself doing life with since #1 and had everything going for him: he was good looking, well dressed, had a great job, owned a beautiful flat, drove a nice car… Personality-wise he ticked all the boxes, too; he was kind, funny, super affectionate and incredibly caring (he was always asking if I needed a drink, or was warm enough, and giving me foot rubs). He seemed like catch of the century, and too good to be true.

And he was too good to be true. One day he called me up at 3pm in the afternoon wasted on vodka at work, barely able to speak… and I realised he had an alcohol problem. “I can be a bit of a mess, but it doesn’t happen often he told me,” so I let that one incident slide, only for him to do the exact same thing when I stayed over the following weekend. He secretly downed vodka and passed out on Sunday afternoon. I couldn’t wake him up, and when I shook him his body was limp. It was actually scary.

I went home and didn’t hear from him for a few days after that. Then he text and told me he needed to get help and I agreed. He vanished for a few more days before popping up like nothing had ever happened.

I knew a relationship was out of the question, but I’d still liked to have met up again as friends, or something casual (I would never seek out something casual, but I had already slept with him and felt really comfortable around him). But when he invited me round for dinner a few weeks later, he didn’t message me on the day and we never spoke again. I was sad, as he was everything I’d been looking for (apart from the alcohol problem) but knew life with him would never have been easy.

#20 (Tinder)

Had some fun phone chats with this carpenter, then he sent me a video of him wanking after I explicitly told him I don’t like dick pics, and it quickly became apparent he just wanted sex. He’s been watching my Instagram stories ever since.

#21 (Tinder)

Went to the pub for a drink with this scaffolder — at the end of the night he told me I was beautiful and that he’d really enjoyed himself and wanted to get to know more better… then the next day he ghosted me.

We rematched on the apps a few months later and he didn’t reply.

#22 (Hinge)

FaceTimed this director/camera man and he suggested we do an overnight trip to Soho Farmhouse for our first date. I told him I wasn’t looking for something causal and never heard from him again. I didn’t fancy him anyway.

#23 (Tinder)

FaceTimed this Irish structural engineer. He had a decent chat, but I didn’t hear from him afterwards.

He popped up four months later asking me out for a drink and I declined because a) he hadn’t spoken to me for months, and b) I could tell he was only looking for something casual.

#24 (Hinge)

Had a lovely date at Soho House with this night club marketing guy. He was super good to chat to and really fit, but just wanted to hook up. He thanked me for a lovely evening, but I never heard from him again.

He popped up on Whatsapp a year later with a low-effort, “long time no speak” message, which I ignored.

#25 (Hinge)

Went to a casino with this boiler engineer and it was probably my second worst date ever. He was super tight — ordered singles when it was his round, then when I offered to get a round he asked me to buy him a double!!! He also didn’t want to spend any money betting in the casino.

When we both needed the loo he said, “You go first so I can look at your arse as you walk…” which gave me the ick. Then he told me he hasn’t been in love for 10 years because he has walls up and that I “should run”. He also said he doesn’t trust women. I didn’t even fancy him that much, so when he asked to see me again, I took his advice and did just that.

#26 (Hinge)

I went on a couple of dates with this property services manager — he was incredibly lovely, nice looking, intelligent, really funny and seemed super sweet. But it got off to a bad start when he lied about his height. I don’t care what height a guy is, but I do care when people lie.

He seemed a little insecure in general and would make comments that came across as down on himself, which killed any attraction I did have. When he asked to kiss me on the second date, I had to say no and later told him that I just saw him as a friend.

Maybe I’ll regret not trying harder with him one day, but I didn’t want to risk leading him on like #5 as he was such a nice guy.

#27 (Bumble)

FaceTimed this property guy — he had amazing energy but seemed a little chaotic. I never heard from him again after the call, and a few months later he was posted on a dating group on facebook, accused of seeing other women while having a girlfriend. Glad I didn’t waste time meeting him.

#28 (Bumble)

This project manager seemed super lovely — he planned an amazing first date for us, with bowling, dinner and roof top drinks, and several more cute dates followed. When I had a bad day he even drove two hours out of his way just to give me a cuddle and bring me some sweets. “This one seems different!” my friends and I said… but then, after five dates, we slept together and his energy immediately changed up. He said it hadn’t and that he was just hungover, but he continued to give me shit energy for another week.

When he became too busy to see me (after being incredibly available before), I suggested we just leave it, and he said, “Yeah I think that’s for the best.” He then gave me some rubbish excuse about having lots going on and being at a crossroads in his life.

He popped back up and tried sleeping with me again a few months later, which wasn’t happening.

#29 (Bumble)

This 40-something tech guy was reluctant to give me his number until we’d FaceTimed. After the call he was acting super keen, telling me I’m his exact type, and that we need to get me off the dating apps ASAP, because he knows what he wants and he’s found it. He also started rolling out the pet names (bubs, baby, beautiful) and, for me, it was just too much too soon.

The next morning he sent me a gushy text which I didn’t reply to, and then a follow-up text a couple of hours later asking if I got his text. I decided to reply and politely say that he was a bit full on for me and we should leave it. He then proceeded to go mad at me, sending me a huge Whatsapp thesis, saying this is why he doesn’t like giving his number out and that I need to work on my people skills…

#30 (Bumble)

Went on a seven-hour date with this American Cambridge criminology student. He was incredibly intelligent and easy to chat to, but there was just no sexual connection. While being mature for his age (definitely more mature than me) he was only 23, so it wasn’t going to go anywhere anyway. We arranged another date, but then the chat just kinda fizzled and I stopped replying.

#31 (Bumble)

FaceTimed this railway electrician — I enjoyed chatting to him on the call, but he gave me dead chat over text after, so I killed the convo and he never bothered to revive it. Sometimes people just aren’t feeling you and that’s fine.

#32 (Bumble)

FaceTimed this data analyst who was really good looking and quickly asked me on a date. Turned out his idea of a date was me meeting him and his friends on a night out they already had planned, so I took the hint and declined. He also popped up on the facebook dating group a few weeks later with the girl posting him saying he had twins (a fact he’d failed to mention to me).

#33 (Bumble)

Really nice guy and quite good looking, but he was a barber, and the entire dinner literally felt like making small talk at the hairdressers. He was a perfect gent though, but clearly both weren’t feeling the spark as we never spoke again.

#34 (Bumble)

This half-Thai sales project manager had amazing banter over text, but he kept making sex jokes so I nearly didn’t meet him. We had an awesome first date (dinner and Fair Ground, and he bought me a teddy which was cute) but then his energy changed up. He asked me to go to his for the second date and I said no, so we went cinema instead. He asked for a third date but never booked it in.

When I asked if he even wanted to go on the third date, he said “If you wanna…” The enthusiasm was too much too handle, so I suggested we just leave it, he replied with “Bruhhhh”.

We rematched on the apps a couple of months later. He tried to get me to go round his again and yet again I said no.

#35 (Bumble)

I only really met this Uber driver because he went to the same gym as me and it was super easy. When he walked over to me at the gym he looked nothing like his photos (he’d gained a lot of weight since they were taken and looked really different). Plus he was quite clear in telling me he only wanted something casual anyway.

He popped up again a few months later and got annoyed at me when I still didn’t want to indulge in something casual with him, and blocked me.

#36 (Bumble)

This Irish guy worked in pharmaceuticals and looked like Colin Farrel — we had a nice drink at the pub, but then he text me after to say he was hungover and he gets horny when he’s hungover, and I never heard from him again. No big loss.

#37 (Bumble)

Gorgeous guy of Iraq/Kuwait heritage who didn’t seem to have a proper job, but enough money to constantly be travelling. We went for a drink and he mostly talked about himself. He was going travelling for a month after our date, so said “stay in touch”, which felt more like networking than a date.

He popped up two months later asking if I wanted to see him again. I kind of did want to, but my uncle had just died, and I knew this guy didn’t want anything serious, so I told him I was taking a break from dating (which I was).

#38 (Bumble)

This guy was lovely looking, we got on great, and had a really nice first date, but the next day I told him I was taking a shower, and he made the classic sleazy comment about wanting to join me, which gave me the ick.

When we went for dinner on the second date, he wanted me to split the bill even though he’d spent way more than me (he was drinking and eating meat) which is a bugbear of mine even with friends.

I had also told him I’d not long got over my ex (this was right after #1 cut me off for the final time and I was a little heartbroken still), so wanted to take things slow.

After only two dates this guy told me I needed to figure out if I wanted a relationship or not because he doesn’t want to waste his time. Which is fair enough, but felt a bit pushy, so I told him I was too busy with work to date (which wasn’t a lie at the time).

#39 (Bumble)

This plumber had the best banter of any guy I’d ever met in my life — it also helped that he was beautiful and looked a bit like #1. We spoke for another week after our FaceTime, texting all day every day, volleying the lolz back and forth, but I quickly realised he had no intentions of actually meeting and was just penpal’ing me so I deaded the chat.

We rematched on the apps five months later and he didn’t say anything.

#40 (Hinge)

FaceTimed this finance guy. He was lovely looking with beautiful teeth, but just a bit awkward and kept saying really cringe-worthy stuff. I kinda knew he wasn’t for me, but would have met him anyway. Despite repeatedly saying he wanted to meet he never actually made plans, which I was fine with.

#41 (Bumble)

This insurance broker was good looking, confident and funny, so obviously we hit it off immediately. The chemistry was mad (always a red flag) and we kissed within an hour of meeting.

The love bombing began the night we met, when he told me: “You deserve the world and I wanna give it to you” and I had to stop myself laughing. “These lines must work on young women, but not a woman in her 30s who’s dated nothing but emotionally unavailable men for two years,” I thought to myself.

He also got drunk and trauma dumped about his mum, saying that she’s evil and she tried to kill his nan (apparently it was in the papers). And he told me he only dates older women because they make his life easier, younger women are always on his case…

He acted the perfect gentleman on our first date, opening car doors, ordering us takeout, but by the second date I was getting my own doors, he told me I had to cook my own dinner and he started smoking around me without asking.

I would have liked to keep seeing him casually, but after he dropped the effort, I didn’t message him for a few days, which seemed to annoy him and then he lost interest.

#42 (Bumble)

FaceTimed this English-Turkish guy who seemed enamoured with me immediately, telling his friends I look like a “Russian model” while we were on the phone and saying he wanted to “breed” me (what am I, a horse?).

I was up for meeting him until he made it clear he needs a subservient woman, who will take care of him, and if I get pregnant with his child I’m not allowed out with my friends. So I told him I’m probably not the woman for him. I thought he’d get mad at me, but he was actually really sweet about it and wished me luck on my search for love.

#43 (met IRL)

This was a guy I’d met through work years ago, and always had a crush on. We’d only actually met once due to him living abroad, but we’d always flirted lots over social media. Eventually he moved back to the UK and asked me to the cinema — I had no idea if it was a date, but assumed it was since he bought me a little gift and paid for everything.

He was the most adorable human, and we had a super lovely evening. He said it was the best night he’d had all year and that he couldn’t wait to go out again (once he was back from a work trip he was going on). But then while he was away, his texts gradually got more and more low-effort, eventually turning into no contact at all, and I gave up on the idea of meeting again.

I was bummed out for a while, but he was a massive weed smoker anyway, which isn’t something I’m looking for in a life partner.

#44 (Hinge)

FaceTimed this 22-year-old mechanic, and he seemed sweet, but the chat didn’t flow that well and he was 22…

#45 (Bumble)

Had good text chat with this nurse, but when we FaceTimed he was being really pushy with his opinions. He said, “You shouldn’t have a fringe because it hides your face… why are you trying to hide your face? Are you insecure?”

Then after our FaceTime I mentioned something I’d seen on Bumble, and he seemed annoyed I’d gone back on there (he told me he wasn’t talking to anyone else) and he stopped speaking to me. Didn’t want to meet him anyway.

#46 (Bumble)

Got on really well with this half-Korean guy because he was also a writer, and he was really funny. We went on a couple of nice dates, but there were red flags: he still takes drugs and goes to raves aged 37, and told me sometimes he’ll kiss a girl at the end of a date even if he doesn’t like her. He also said he’d only go on a date with a girl he wasn’t sure about if he “wanted to get some”. After that I realised he just wanted sex and we never spoke again.

#47 (Hinge)

This English-Lebanese guy gave off fuckboi vibes from the get go, but he was super intelligent and funny so I met him anyway. The chemistry was insane (as I said, always a red flag) and we had an amazing first date.

When we spoke on the phone for seven hours the next day, I knew I was being love bombed again, but I was bored and I really fancied him, so I entertained it. He also sent a dick pic after I told him not to, and gave me flashbacks to #1 when he said “girls always fall in love with me”. Okay, hun.

He chatted to me every day for a week, and then the night before our second date was due to happen, he called me up and told me he wanted to end things because I “don’t chase him enough”. Considering I’d been on the phone to him all day every day, I found this to be an insane statement, we got into an argument about it and he blocked and deleted me.

He then popped up a few days later like nothing had happened and I went on the second date anyway (I know, I know, I shouldn’t have gone, but I was bored, and the chemistry was amazing). I was playfully winding him up about how he’d tried to give up smoking weed and caved after three days, and he got annoyed and shouted at me. I knew I couldn’t realistically continue to date him after that; shouting is a hard no.

The next day, though, he was acting super into me and sent me a photo of the vegan lunch he’d bought (when you are vegan love-bombing men always try and impress you by eating vegan food). But then later that night he told me I was his “favourite ting” and I’d moved to the top of the leaderboard of all the girls he was seeing. He also said he wants three baby mums and I could be the first. I wasn’t sure if any of that was actually a joke, so I cooled off the chat and we stopped speaking.

A few days later he posted an Instagram story of him on a date with a girl, and then the same thing with a different girl a few days after that.

#48 (Hinge)

I FaceTimed this events planner and he seemed nice, but to be honest, I felt so broken from dealing with the previous 47 men, that I just couldn’t even be bothered to take another man seriously. He was really busy with his job anyway, working days and nights, so he never actually planned a date in, which was probably for the best. And not surprising, since I suspect I was giving off major man-hating vibes at this stage.

Dating in Dubai

Towards the end of my dating journey, I went on a solo trip to Dubai, where I met four guys. Obviously all a waste of time since they live abroad, but good for the plot as they say.

#49 (Hinge)

The first guy was an Italian architect, who told me to meet him at a club because his friend had a table. He took me inside, dropped me off at the table (which had been purchased by a wealthy BA pilot) and he disappeared. He re-appeared half an hour later with more girls in tow, asked if I was okay then vanished again. Clearly he was some sort of recruiter for the BA pilot.

When everyone went on to a new club at 2am, I went home, and the architect text me at 5am saying he wanted to watch the sunset with me. I ignored it and he unfollowed me on Instagram.

#50 (Instagram)

This Swiss watch dealer said he found me when I popped up on his Instagram discover page. He was super lovely, sent a car to pick me up, and bought me dinner and drinks at a really nice bar. His chat was great and we got on super well. But then he dropped me back to my hotel and I could tell he wanted to hook up. I found him attractive, but didn’t want to sleep with him, so I declined his invite to go to a beach club the next day and the chat died out.

#51 (Instagram)

Another Swiss guy — this time a moto racer — found me on Instagram because we were in hotels next door to one another and I’d tagged the area we were staying in. We had a fun night exploring Dubai Mall and taking a trip up the Burj Khalifa. Since I didn’t really fancy him, and didn’t want it to be a date, I offered to pay my share of everything and he let me.

When he tried it on at the end of the night, I said: “I’m not going to sleep with someone I’m not dating…” and he replied, “But we did go on a date?”

“The guys I date usually pay for the first one,” I said. “Oh, don’t say that!” he said. “Now you just sound like one of these Dubai women… A good girl will always offer pay her half.”

He tried it on the next night after that too, and when I Googled him it said he earns about 130K a year haha.

#52 (Hinge)

The final guy I met in Dubai was a Swiss-Afghani footballer, who was ridiculously good looking and well-dressed. I went for a drink with him and his friend, and he was super sweet (he wanted to FaceTime before meeting to make sure I felt comfortable with him, and kept telling me how young I looked for my age).

I had a lovely evening with him, but it was obviously never going to go anywhere. Still, his compliments were a nice little ego boost before going into dating retirement I guess.

The final straw

I spoke to one final guy when I got home from Dubai, who was left over from before — he was Turkish-English, and initially annoyed me by inviting me to his house for the first date. I decided to ignore that one red flag and give him another chance as he seemed really intelligent and only lived 10 mins away.

But he made some possessive comments, asking if I was talking to any other guys because he “doesn’t like to share”, and questioning if I even went to Dubai alone or if I’d gone on holiday with a romantic interest. He also made a joke about wanting 10 kids with five baby mums which reeked of #47.

The final straw was when he made a cruel comment about me having lip filler. “I stalked your old photos, so I can see why you needed it,” he wrote, followed by a laughing emoji.

He hadn’t planned a date in anyway, and seemed to be penpal’ing me, so I just stopped replying.

So now what?

For now, I am done. I’m a strong woman, who has gotten through a lot of hardship in her life, but dating men in this generation has truly broken my spirit and made me question my self-worth.

You need titanium self-esteem to deal with constant rejection, ghosting, love bombing, disappointment, disrespect, emotional unavailability, psychological issues, and general mean comments (I’ve received actual verbal abuse from men I chatted to on dating apps which I won’t even go into here).

Of course, I played my part in allowing myself to be treated poorly. I gave way too many chances to guys who had already shown me they didn’t care (#1), ignored plenty of red flags and dated guys who were way too young (not that the older ones behaved any better).

But the fact is, there’s a scarcity of a good men who are single in their 30s — and I always had a tiny grain of hope that “this one might be different” and “things might finally work out”. And the ones I knew were inappropriate off the bat? When you’ve been single for three years, sometimes you just need a cuddle from someone you find attractive.

But the experience has left me heartbroken.

Not over any of these men in particular, but heartbroken for myself, and how hard it is to find love in the modern age. Heartbroken at the loss of the future I’d always imagined for myself: meet a great guy, fall in love, build a home and start a family together. Grow old together.

There are serious limitations to not finding a life partner: my life is devoid of regular affection and sex; I spend most Saturday nights alone because my friends are busy with their partners and/or kids; I have to travel alone and everything costs me twice as much because I have nobody to split it with; I’m stuck living with parents in my 30s.

And having children? Well that isn’t even an option for me as I don’t want to raise a child without a father. Nor do I have the money/energy to raise a child alone, before people start piping up with “Why don’t you go to a sperm bank?”

Friends, family and strangers might throw empty platitudes my way (“You’ll find love when you least expect it… you’ll meet someone soon as you stop looking… there’s someone out there for everyone…”) but there’s a real possibility that I might die alone.

And it’s time to accept that. Dating is different to how it used to be. Men don’t feel the need to settle down when casual sex is so freely available. Monogamy and marriage are becoming antiquated concepts. Everyone in the dating pool is disillusioned, burned and broken from previous experiences. Myself included.

So I will just have to do me. I’ll pour my love into the people who do see my value (my friends and family). I’ll fill my life with hobbies and solo dates. And I’ll trust in the universe that it won’t completely fuck me over when it comes to handing out life partners.

Ty for reading 🩵

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Jennyfer Jay

Sharing everything I've learnt about healing and glowing up