A Single Mum’s Diary of Dating Horror Stories

There comes a time in one’s single life, even as a busy mum, that you decide to ‘put yourself out there’. I did. Several times. I now have a diary of horror stories to tell. Oh and I’m still single..

Diary Introduction

I will start this by saying I work full time as a child care Director, I have my son with me 12 days out of every 14 days, I have side hustles, and I’m trying to build my own business with this blog. I therefore have minimal time for dating and meeting new people. So I joined online dating sites and published an enthusiastic profile, deciding to ‘give it a go’. On the few occasions I have decided to put in the effort, spending way too long deciding what dress, what shoes and what lipstick, I unfortunately have been sorely disappointed! Before you decide to challenge me and tell me your dating horror stories are worse, read on, put yourself in my shoes and then let me know in the comments if yours compare.. Here are my 5 best (worse) stories..

Single Mums Diary of Dating Horror Stories

1. Judgemental Vegetarian Guy

So we decided to meet at a noodle restaurant and he seemed polite and friendly enough initially until he asked what I would like to order. I had decided upon the chicken teriyaki noodles with veggies but unfortunately, he had an opinion on that! Eric proceeded to lecture me on why eating meat was bad for my health, as well as for the environment and started telling me about his vegetarian diet, how healthy he was, why a vegetarian diet was better and how if he ever had kids one day, he would be making sure they had a vegetarian diet too.

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No, I didn’t walk out immediately, after all I was hungry and I thought I might as well give him a chance to redeem himself in further conversation. In further conversation surrounding foods, I informed Eric that my son was actually anaphylactic to peanuts, cashews and pistachios. Eric asked me if my son was immunised to which I replied, ‘Yes, of course’. Eric seemed to have many opinions on a wide array of topics, and asked me if I thought Andy was anaphylactic because I had vaccinated him? I quickly replied ‘No!’ and proceeded to remind him of the industry that I work in, of my qualifications as an Early Childhood Teacher and the fact that I would always be pro vaccinations! Eric then started lecturing me on why he thought immunisations were unnatural, unnecessary, probably caused autism, as well as allergies and anaphylaxis and then had the nerve to mention, “I just thought it was better that you know where I stand on Immunisations, so that if we ever have kids one day, you know how I feel, because I will never be immunizing my kids.”

Under my breath I mumbled to myself, “We are NEVER getting to that point Buddy, let alone to the end of this meal.” After downing my food super quickly, Eric asked me if I would like to go somewhere for dessert, to which I said, ‘No thank you’ and rushed back to my car at lightning speed, with no intention of ever speaking to him again!

2. Hungry Guy With No Wallet

Mike seemed lovely in prior texts and conversations and was very good looking in his photos! I was excited to meet him, but unfortunately he looked NOTHING like he did in his photos! It was clearly the same guy, but let’s just say his appearance had altered a LOT and the photos were clearly quite old. Despite this, I was more than happy to give Mike a chance. We started ordering dinner. I ordered the prawn salad with some garlic bread, and Mike asked me if I would like to share a few items. I answered, ‘Sure, why not!’ and Mike then proceeded to order; 2 garlic breads, 1 large pizza, the prawn salad, a side of chips, a side of veggies, a chicken schnitzel and a plate of salt and pepper squid. Just for the two of us. No, I’m not even joking.

Single Mums Diary of Dating Horror Stories

When the food came, I thought there is no way we will get through this, so I hope he is hungry. Hungry he was! I nibbled at a few things but was not really too hungry to begin with. He polished it all off while telling me about his job as a nurse and the fact that he only works night shift, so he sleeps all day, and works most nights, all through the night, sleeping all day and with only one day off per week. While I was sitting there pondering the fact that our work/free time schedules would never work together, Mike reached into his pocket and… with a horrified look on his face, told me had LEFT HIS WALLET AT HOME!

I rolled my eyes on the inside and went to pay the hefty bill. I went home and decided we had very little in common and was very put off by the whole thing. I guess I’ll never know whether the wallet at home thing was actually deliberate or not, but I certainly didn’t want to even give him the chance to ‘return the favour’.

3. The Plumber Who Got Too Excited

Now Simon was actually very polite, good looking, seemed to have a good job running his own plumbing business and while he spent most of the date talking about himself, telling me about his 3 kids, his past relationships, his work issues, his family and his health problems, the date wasn’t all in all, that bad. He took a breath here and there to actually ask me about what I do, about my son and about my past dates, but for the most part loved talking about himself. Now, the date wasn’t awful, just a little one sided but it wasn’t until I got home that he really turned me off!

Single Mums Diary of Dating Horror Stories

Once I got home, he started bombarding me with THOSE kind of pics.. yes, DP’s. In all its glory. He started telling me that he just wanted me to see how ‘excited’ he was to see me, he wanted to ‘prove’ how much he liked me and wanted my opinion on what I saw! Now, I think I speak for all women out there, EW!!! We don’t want to see DP’s from guys we just met, or guys we don’t even know. It doesn’t turn us on, it doesn’t make us like you more, it has the opposite effect. On the drive home, I was pondering as to whether I would agree to see this guy again or not, and then with these explicit pics, he made my decision for me! It was a NO from me. I blocked him on the dating site, but we had swapped numbers so he started bombarding me on all portals – by text, by Whatsapp, he found me on FB and started sending the pics through there too! I had to block him on all fronts and again, realised I was far from finding the man of my dreams!

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4. The Gentleman with a Potty Mouth

Carlos was hot stuff! He was South American, had a hot accent, smelled so good and I was attracted immediately. We had dinner, he was beautifully polite and a gentleman who had lovely compliments for me! We talked a lot, we laughed and we swapped stories about our families, about our work life and about travel. The date was good! He offered to walk me back to my car after the date and I was happy for him to do that. We shared a kiss by the car. Carlos wanted more. And now. I was happy to share an after date kiss but as for more, I said no. Carlos persisted but I politely made it clear that in this moment, it wasn’t going to be more than a kiss. I was open to seeing him again but I was not open to getting more physical with him in this moment. He accepted my decision and left.

Single Mums Diary of Dating Horror Stories

When I got into my car after he had left, the text messages started. Carlos actually told me he had never been ‘rejected’ like that before and began to verbally abuse me with a string of messages, questions and comments. I was shocked! The words, the profanity and the insults were fast and incredibly abusive!! I couldn’t believe how aggressive he was!! The messages were coming faster than I could even process them and think about blocking him. I think in the space of about 10 messages, he used every profanity I can even think of, accused me of horrible things and even threatened me. I was so quick to delete him and block him in a panic to not see any more texts of this type, it didn’t even occur to me at that time to report his behaviour to authorities as being abusive and threatening.

Clearly this guy had some serious issues, and I no longer allow guys to walk me to my car unless I have had the opportunity to get to know them a lot better.

5. Curious George with No Shame

Curious George was a little too curious! His name was David. We had a couple of drinks, we had some dinner and the ‘get to know you’ questions started. The questions started off pretty tame but they became more and more intrusive!


I made it clear to David that there were some questions I was just not comfortable to answer but he wanted to know Why!!

David was just a perve! David had no shame and began asking SUPER personal questions – not even things some of my best friends I have known for years would even ask me! I made it clear that I would not answer these questions about my past dating life, about my past physical relationships, about what I like to do when I’m in an intimate relationship with someone, or what I don’t like to do! I started to pack up and leave because he wasn’t taking the hint, and he continued to ask, maybe to see my reaction?! Of which I was remaining pretty neutral, not giving him what he wanted which I believe was the shock factor or even some type of answer. He didn’t seem to understand why I was getting uncomfortable and did not respect my boundaries. He remained at the bar as I packed up and left, again deleting and blocking someone from my phone.

Diary Conclusion

Despite these stories, I will continue to date, have a social life and I’m open to meeting new people. I have just come to the conclusion that the dating world IS full of freaks and weirdos and it can take time and effort to sift through them!

I am always an advocate for taking care of ourselves, physically and emotionally. Sometimes that means staying in and having a quiet night alone, but sometimes it means making an effort to have a social life and meet new people. I have some helpful tips for other single mums in my article;

‘How to THRIVE, not just Survive, as a Single Mum. It includes prioritising a social life, whether it’s with friends, or by putting yourself out there to meeting someone new by braving the dating world.

I hope my stories make other single women or single mums out there realise they’re not alone! Many of us have dating horror stories and hey, they can sometimes be a great ice breaker on a new date! ; )

If any single mums out there need further support, you can try the Raising Children website for further info and helpful resources;

Do you have any stories that you can share? Keep them PG and let me know in the comments! I would love to hear them!!

4 thoughts on “A Single Mum’s Diary of Dating Horror Stories

    1. Hahaha thank you Nicole! Oh, there’s so many creeps, weirdos and unhinged men! I’m sure there’s just as many weirdo women out there too but yes, I’ll persist! Once Sydney is out of lockdown anyway!

  1. Oh my god, I think I could write a whole book on my dating mishaps. 🙂
    But your vegetarian story… well I am vegan, and at some point I felt, ok maybe I try dating the guys who are vegan as well. I signed up to a vegan dating forum on facebook and went out on few dates.

    1. The guy claimed he was a minimalist. He lived on the floor in his brothers kitchen. He invited me for a dat to a walk. OK. then we got really cold as it was close to zero, so I suggested we go for a coffee. He picked out his own mug self made from thrown away jar wrapped in aluminium foil. Really cool guy, but when I started to think that I would be living with a leech, I thanked him.
    2. this guy actually lived next to me, and we matched on tinder. I clicked on him because of the vegan thing. He then started to talk about himself. ALL THE TIME. I was suggesting we go for a cup of tea somewhere in the gas station nearby, or something. He always had some idea on why not. I said I want to be just friends, and meet new people. Anyway he called me a judgemental person, who should maybe go and get some education, and he is not going to deal with me. I said, maybe if you would have paid a little attention to ask who I was, you would realize I have a PhD, so I don’t think I need more education.
    3. This guy walked me through the whole city in search for some specific cherry icecreams for vegans run by Robert’s coffee (kinda like starbucks). We didn’t find them. Eventually we ended up in a cafeteria, in which he pulled out his pokemon game to check how many pokemons he caught on his walk…..
    4. This guy apparently has been for a year at home during covid. Not leaving his home. He has written to me on facebook a year before, but I was dating one guy then and I just ignored that message. I found it when cleaning my phone and i wrote him back. Ok, so we decided to meet up. I made banana breads, and made soy milk. We agreed to make a picnic. And I came there to find out, he was afraid to be going around so that people wouldnt like to buy from him. It turns out he was growing maryJ in his appartment in the past, got caught, had a probationary sentence and since then just stayed at home. Apparently, never had kids, never married, bla bla… and at some point he got up and said that he doesn’t like me because I remind him very much of his mums friend and she doesn’t like her children, so he will go home now.
    5. This guy was a civil engineer in one of the cities in metropolitan area, dealing with roads. I figured, hm, we will have something together, and we can maybe kick it off. From the moment we met he kept commenting on my boobs, how large they are, how probably there was many men who have pleasured themselves etc. I thought it was just joking. But basically at the end of the evening he started to get closer and grabbing my boobs and so on. I tried to kiss him. He run out. I tried again, he run out. I said what the actual F…. and he said “Well, I don’t want to take advantage of a woman” (while holding hands squeezing my boobs as a stress toy). “You probably don’t understand. You have been dating non-vegan men. They have different morales. I am vegan I am having stronger moral backbone” (still squeezing my boobs).
    That was the first time I started shouting at a stranger man and throwing stuff at him 😀 I am not proud of this, but it just tipped the scale.


    To quote Carrie Broadshaw from “sex and the city”, – ‘going on a date with a guy older than 36, is more like trying to figure out “what is your defect that all the other chicks rejected you before?” ‘

    mic drop.

    1. Oh my goodness, your stories!! Thank you SO much for sharing, I’m not alone!! That is somewhat comforting but I’m so sorry you experienced those dates.. Haha, at least they are ice breakers for new dates. I’m happy you found enjoyment from mine.. at least as bad as the dates were, I got a blog post out of it!! Hahaha.. thanks Mum Investor! Take care.. E.

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