Harrowing, hilarious, lonely and exhausting: The undeniable truth of dating in 2020.

"Dating over 30 is like going to the dump and trying to find the least damaged and broken thing possible." - Mia.

"I go on a date almost every night. It’s a sport for me. Dating is a numbers game." - Bushra.

"In 10 years, my son has only met one of the men I’ve dated, and no one has ever stayed the night." - Nama.

"Now I’m older and more comfortable in who I am, my dating outlook is less ‘I need to meet somebody’ and more ‘whatever will be, will be’." - Sarah.

This is just the tiniest sliver of what came back to me when I asked 11 women to describe dating in 2020.

From the harrowing and hilarious to the exhilarating and exhausting, what is it actually like deep in the dating trenches?

Below, you’ll find a curation of short stories from people who identify as female on their unique dating reality. 

Because even though it’s Valentine’s Day - a day full of Hallmark cards and hand-holding and roses being delivered by courier - love and dating isn't rosy for everyone. 

In response to the difficulties that come with modern day dating, Mamamia has launched Eligible, the world's first podcast dating show. Post continues after audio.

Each of the women we spoke to has their own outlook on dating and the role it plays in their life. For some, their words will shed light on a completely new perspective or an experience you’ve never thought to consider. For others, they’ll speak to the small part inside all of us that's convinced that maybe, deep down, we're the problem. 

But when brought together, these stories point to an undeniable dating truth: even though it’s never been easier to find someone in 2020, finding ‘the one’ has never been harder.

Just a note: The women who shared their very personal stories with us are known to Mamamia, but have chosen not to share their images. 

Bushra, 29.

I am a Serial Dater. 

That’s what my friends tell their friends. And their friends’ friends. I go on a date almost every night. It’s like a sport for me. If I could liken it to any one sport, it’d be golf. Because there are red flags everywhere. If you manage to get past those flags, which is rare, you’re going to have to keep whacking those dimpled balls until you get a hole in one. They say it’s about the journey, not the destination, right?

I’ve been dating on apps on and off for years. (Meeting someone organically hasn’t exactly worked out for me, the last time I asked a girl at my local pub for her number, she gave me one with too many digits.) 

Over my many moons of dating, I’ve come home with some great stories. The Catfish. The Racist. The Secret Parent. The One Who Needs a Therapist and Not A Date. In hindsight, I probably ignored red flags, but I don’t anymore.

Bad grammar? Red flag. Too many cry-laughing emojis? Red flag. Asking me where I’m from “originally”? Red flag. Still lives with her ex girlfriend? RED FLAG. Of course, dating can be a bit disheartening and you have to be ready for rejection at any point. 

Although some of my experiences have been shocking, it’s not all horrible. As a woman who dates all genders, there’s a lot of people to meet and find common ground with. I’ve met great friends, and people whose perspectives have been eye opening. My bad dates also make for excellent content for my friends. And sometimes, you even manage to stumble on a rare gem who will make your IKEA furniture for you.

Mia, 34. 

How do I feel about dating, in one word? 


I'm almost 35 and have lived in a regional center (population of roughly 40,000) for many, many years. I love the country, I have a terrific, supportive network of local friends and my family isn't too far away. I enjoy my job. But I don't enjoy dating. Dating is hard.

After sorting myself out and getting myself emotionally ready to be in a relationship, it feels like all the good men are gone. Most of the local men out here married their high school sweethearts, or have had messy divorces that fuel relentless small-town gossip. Once, I went on a date with a guy in another town four hours away. Two days later, my neighbour introduced me to someone as ‘so and so’s girlfriend’. 

I’ve been speed dating in the city but most men switch off as soon as I explain where I live. Other times, men I’ve met online insist on visiting me, instead of allowing me to meet them in more metropolitan places. They book their stays for three or four days, with the "no pressure" clause added in. When you realise there's no chemistry an hour in, four days is a bloody long time to entertain someone in a small town. It's also awkward to navigate the introductions and follow-up questions when you run into people down the street.

Then, there's the well-intended but hideously misdirected setups you get when you’re the town “victim”. The tragic single. "You would be perfect for my neighbour Gladys' great nephew's second son, Peter. He's very rich and lovely, he just wants a nice woman to settle down with." 

I've chosen to live regionally and I've never regretted it; but I'm tired of dating. I’m more than a little lonely. I'm grieving for the children I might never have and struggling to accept that I had many opportunities to date wonderful men that I didn't take.

Charlotte, 46.

Roger asked me to leave at 5am. He decided I “wasn’t his thing.” He was keen to catch up with me later as friends, though. I felt so special. Chris didn’t reply for a terrifying 15 minutes when I told him by text. I was about to block him when he sent through a shrug emoji; he didn’t mind. Greg and I hit it off when we first met over drinks in a bar. He was keen to meet again; another drink in the city sometime this week even. So I told him about my gender history. I heard nothing back.

Dating as a trans woman is largely the same as dating as a cis (when your gender identity matches the sex you were given at birth) woman, but with some key differences. By dating me, you are dating an especially vulnerable person who wants to receive (and give) love and respect. 

I also have to deal with bigots who’re increasingly emboldened to voice their hatred of who I am. They’ve moved on from marriage equality. Gender identification and transgender people are the new conservative punching bag. 

Equally, there can be a lot of acceptance... if you “pass” well. By pass, I mean to look like a typical ‘woman’. Some men are happy to keep me as their ‘little secret’, but some won’t introduce me to their family and friends because of the collateral transphobia they will face. 

The dating game for trans women is probably more encouraging than ever, but our Western culture still has a long way to go. And like all dating for all people, when you put your heart on the line with a stranger, it’s still a minefield of rejection, hurt and real physical danger to find the gems that are out there.

Sarah, 30.

I’ve been dating regularly for almost seven years. 

I’ve also had vaginismus since I was 16. 

For context, my vagina and I have never been mates. I’ve got vaginismus. I‘ve had vulvodynia. I don’t get dermatitis anywhere on my body, except on my vulva. I also had surgery to remove my imperforate hymen that made sex feel like losing your virginity over and over again. 

Dating with sexual dysfunction can make you feel humiliated by your vagina. 

On the flipside, I’m very skilled at giving an amazing blowjob.

Because of my sexual dysfunction, casual sex has a negative connotation for me. You’re constantly debating with yourself: am I comfortable to open up to this person? Will they understand? Will they hurt me? Do I disclose my condition or not bring it up? Recently, I had a great experience with a man I slept with who completely got it and was really invested in making sure I was OK and enjoying it, but that’s not the norm. 

I think how a person responds when I tell them about my condition qualifies the buyer - if it’s an issue, they’re not the right person for me. Some people I’ve dated treat me like I’m hard work after I tell them about it. Others simply can’t comprehend it. I once allowed a guy to touch me sexually after around five dates, and I now call him the Finger Banging Bandit because even after I told him to be gentle, he just kept ramming his fingers inside me. 

Sexual dysfunction never 100 per cent goes away. It always plays on my mind and adds an extra layer of self doubt to every encounter. If a friend slept with someone and never heard back from them, it might not be a big deal. But for me, sleeping with someone is really opening up to them, so if they disappear after, I feel like shit and wonder, am I really that broken?

There have been times in the past when I’ve been so disheartened by dating because all I wanted was to find somebody and I felt like my body was getting in the way of that. Now, being a bit older and more comfortable in who I am, my dating outlook is less ‘I need to meet somebody’ and more ‘whatever will be, will be’.

Minty, 26.

For me, dating with a disability is exciting. 

It’s fun meeting new people, but dating also makes me perpetually nervous. 

Meeting people “in real life” is actually more difficult than using dating apps, for me more so than most. My disability is noticeable (I have cerebral palsy so I’m usually with my walking sticks) and while that might not necessarily be a turn off for some people, it definitely creates a barrier. Some people also might not want to talk to me for fear of offending me. 

I make mention of my disability on app profiles, but dating online lets me get to know someone without my disability being the first thing they notice about me. I’d tell them anyway, and if they then decide they’d rather not date me, it’s annoying, but also not my problem. I’ve had a hilarious variety of responses from people when they find out I have a disability. Ghosting. Inappropriate questions - but like, can you have sex? Then there’s the people who are genuinely interested and have a complete lack of concern. 

Dating disabled also comes with stigma. It’s the idea that because you're disabled, you apparently only want to date other disabled people, or you're somehow expected to settle for less because you are disabled. I also know a lot of people who do settle. What makes dating easier for me is caring less about the outcome and just going into it as my complete self. If it doesn’t pan out, what can you do? 

It took me a very long time to not see my disability as a reason for people to find me ‘undesirable’ and excuse some frankly disgusting behaviour on or before potential dates. Sure, I have this extra difference - this extra thing - some people might see as a reason to count me out. 

It’s not the only reason I haven’t been asked for a second date, but it’s a part of me that can’t be changed. And if you don’t like it, you’re not the person for me.

Nama, 43.

While I’ve dated quite a bit, I’ve been technically single for about a decade. I’d like to make a MAFS joke and say it’s because my son, who’s now 12, is called “Cock Block”, but really, he’s not personally the reason at all.

I know many excellent dads and men and women who’ve re-partnered happily. But from my perspective, we hear stories all the time about how predators who commit sexual offences against children operate. They ‘groom’. It’s the swim coach. The childcare worker. Men you date who seem wonderful, until they aren’t. I’ll make it clear, it’s not all men. But it’s enough men to justify my decision not to involve someone in my family life whilst my son is still a child.

The stakes are very high, and I don’t have the time, nor the inclination, to put in the effort to sort the good dudes from the bad guys until my son is much older. And for this reason, my son has only met one of the men I’ve dated, and no one has ever stayed the night. It is not worth the risk, and a lot of other single mums I know agree.

For that reason, I have vehemently and deliberately rejected the immense societal expectation to re-partner. To be honest, it’s not been hard. It’s not difficult for me to prioritise my son, even if it means some small personal sacrifices. It’s just another part of motherhood; especially single motherhood.

Does this mean I might have denied my son the chance to have a brilliant step dad in his life? Maybe. But that’s also underestimating my parenting, because I. Am. Enough. And does it mean I have stopped relationships from becoming too intimate? Yes. But that’s OK. Because right now, it’s my job to make whatever sacrifices I feel are necessary to protect my son in his own home. That is my job.

Being a parent is a lot about anticipating risks; and with all the information out there, I’d be a fool not to. If you think I’m living in fear and don’t trust my own judgement, you might be right. But at least my son will be safe in his own home during his childhood.

Leigh, 58.

I’ve been dating for 20 years. But dating in your 50s is a completely different game.

In my 40s, I found myself single raising two small children who needed everything from me. I’ve wanted a man to swoop me off my feet and give me a ‘white picket fence’ since I was 16, but when I got divorced, I realised the world didn’t work like that anymore.

The first hurdle was figuring out how to date people online. I felt stupid, but it was learning things like: how to find things on Google. How to sign up to a dating website. How to upload an image. How to take a selfie. 

I met a lot of people dating online, and in my 40s, it was fun. Mostly. When people would want to have sex with me on the first date, it was exhilarating. But afterwards, I felt worthless. I also made mistakes introducing my kids to the men I was dating too soon. The impacts of those decisions have lasted far longer than any relationship.

Now I’m in my 50s and the way many men respond to me online has changed. The pool is much smaller and filled with men who are older than me. I’ve been on dates with some men who just want to take care of me. Instead of meeting for a coffee, they want to wine and dine me. They say they’ll take me on spontaneous holidays or buy me expensive things. They don’t want me, they want someone to own. 

Not everyone is like this though. I’ve met some wonderful people through dating, but I believe the universe will bring the right person to me when I’m ready. That’s one thing dating is really good for - teaching you about yourself. I’m hopeful I will meet someone, but I’ve also been happy on my own for so long, I won’t settle.

Berne, 24.

Dating for me has always been uncomfortable, but I do it anyway because I crave companionship. 

Then, there’s particular challenges that come with dating with a mental illness. I was diagnosed with Borderline Personality Disorder (BPD) about a year and half ago. 

BPD is not a well known mental illness and the traits can be very different for different people. Google dating with BPD and the first thing you will see is: “people with BPD tend to have rocky relationships, romantic or platonic” because of their “erratic behaviour” and “emotional instability”. I battle against stigma everyday, and dating when the whole world thinks you are an emotional monster is challenging at the best of times.

I use dating apps like Tinder and Bumble. To be honest, they make me feel better about myself. Right now, I have about 800 matches, and knowing 800 guys out there think I am somewhat attractive really helps my self-esteem. The back and forth, the banter, I find entertaining. I’ve had a lot of sex with randoms off dating apps. Sex is easy, you don’t have to reveal much about yourself, and most of the time you won’t see the person again. And in some ways it fills the emptiness of not having a companion.

It gets complicated when I start liking someone because that’s when I start being hyper-aware of my behaviours. Like everyone else, if a date goes well, I get excited. It’s also when I start fighting against my own thoughts. It’s a shit storm of trying not to idealise a person, pushing back thoughts that I’m not good enough, and trying to not get attached too soon. 

For me, the internal conflict is always the most excruciating part of dating. I want to show who I really am, but will you accept me for that? I am a resilient person and I don’t let my mental illness define me, but I still often feel so lost and somehow erased. As if I don’t deserve to be loved.

Zen, 32.

I’ve made it very clear to the people in my life that I do not want children. 

I also make it very clear on my dating profiles: ‘If you have kids or want kids, do not swipe for me.’ 

I’ve been single for 10 years, I’m not here to waste anyone’s time. And something I’ve found through dating is there’s nothing wrong with telling people what you want and what you don’t want. That’s part of what makes dating hard in your 30s, because you do know what you’re not willing to compromise on. For me, it’s children.

Whether it’s in a text message or during a first meeting, I do my best to bring it up in conversation so it doesn’t get to the point where feelings are involved. But before it gets to that stage, quite often people match with me online just to probe me on my decision, as if I owe a stranger an explanation as to why I don’t fit what society perceives to be the normal life timeline for a woman. Or they’ll try to talk me out of my decision, like, ‘oh, when you meet the right person, that’ll change your mind’. It seems most people can’t comprehend that a female could not want kids. 

Recently, a horrible experience forced me to make a choice to no longer actively pursue finding a partner. I’d been on a few dates with a guy and it was a non-issue for him that I didn’t want kids. Then, on the fourth date, he told me he had a 12-year-old daughter. To be disregarded in that way… it happens quite a lot, but that was the last straw.

I know my life decision contributes to me not being able to find someone. But it’s gotten to a point where I’m completely drained and disheartened by dating. I used to track my first dates and at one point, I’d been on 17 dates in 12 weeks. And when you’ve gone on 17 first dates and few turn into a second, a third or a fourth, you start to question whether you are the problem. 

My ultimate goal is still to find someone I can share my life with, but there has to be a point where you have to take care of yourself first. A point where you think, ‘maybe this isn’t going to happen for me…’

Sam, 34.

Although dating can be tricky for anyone to navigate, I truly believe being a plus size woman comes with more dating challenges. 

One of those challenges is the role your weight plays in relationships - my body is the third wheel in many of my dating interactions, for many different reasons.

Many of the men I’ve met online fall into two categories. The first are those who tell me they find my curves appealing within the first few messages. My photos are recent and show my entire body in a variety of angles, and I used to announce my size like you would your age or occupation.

‘Confident plus size babe here, swipe right if you like curves.’ 

The second are the ones who offer to be my personal trainer. Weight-related jokes, and any other behaviour rooted in fatphobia are not tolerated, but it happens. I’ve had to learn how to date in a way that empowers me, not brings me down. 

Fat women should enter the dating arena with confidence, a vision for what they want, and tools that will help them find a partner who loves, cherishes, and respects them — and their bodies. I’m confident that I will meet the right person for me, who loves and respects me for who I am.  But right now, I’m in the frog kissing stage and hopeful that my prince charming is on his way.

Rhi, 31.

I’d tell anyone to give dating apps a try. They’re a great way to get your confidence and see what’s out there. But you might not necessarily like what you find. Here’s the perfect example: 

I matched with this guy and was having some general chit chat. He seemed nice. He mentioned he was playing golf this weekend, and after I politely replied that sounded like fun, he said: “Cool, well if you like golf, how about I fill up a condom full of golf balls and fuck you with it?” 

I feel so many things about dating. I enjoy it (or at least I do sometimes), but even when you’re enjoying it, it can feel like you’re interviewing all these people to see if you have a spark. I find it empowering to pick and choose who I want to meet up with, but it’s also a drain on my energy and time. Most days, by the time I’ve gotten home, I’m asking myself, do I really want to spend my very limited time getting a drink with some person I’m not even sure I’ll like, or with the important people in my life? I’ve had some dates that were horrendous, but most of the time, at the very least, you meet a nice person who you connect with in some way. 

If you come home from dates and always see it as a waste of time, you’re only going to feel negatively about dating. You’ve got to try and give it a positive spin. Like, now I know I’m not into X, Y and Z, or I learnt something about this. Or at least I got a free drink at a cool bar I can go to again. Yes, I’d like to meet someone, but I wouldn’t say I’m lonely. 

I’d rather be single than be with someone just to be with someone.

Thank you to all the women who shared their experience of dating with us. 

Top Comments

Guest 2 years ago

Trying to avoid the married men is the hardest part of online dating.