Trying too hard

He was wearing a suit like the rest of them.

He was talking so animatedly with a total babe of a woman that I thought they must have known each other. She was laughing a lot. Turns out they’d just met earlier in their six minute ‘date’. We talked about the finger food and I slipped away to check my phone in the loo. The mingling at the start of speed dating is fine, you can just find another woman who has rocked up alone and talk about dating. But by intermission it seems everyone has found someone to yarn to and I just felt like a social break.

When I finally got to date him, I think I had just asked a few dudes what made them happy so to mix it up I asked what really pissed him off. Cue anecdote about noisy neighbours. Look, he didn’t ask me a great question, and it wasn’t an amazing story, but he did know how to tell it well and I laughed. Tick. He maintained eye contact and didn’t compliment me creepily. Tick tick. Even though I spent ages deciding what to wear (and modelling different options for my housemates) I’m always a bit turned off when one of the first things a dude says is about how I look. I don’t really understand how that works. Maybe it’s that I want them to notice, but I don’t want it to be the main thing they notice enough to compliment, within the first six minutes of meeting? The very first thing another guy earlier that night said was that I had a pretty smile, then that my dimples were cute, then a few minutes later that I had nice eyes. Maybe I am trying so hard to play it cool and pretend that we aren’t sussing out each other’s physical appearance and that we’re genuinely trying to determine the potential for a deeper connection, so when someone smashes that façade it’s a bit jarring. Maybe everyone is a bit weird about accepting compliments. Also – it’s not a conversation starter. All I can respond to “I really like your eyes” is “um, thanks.”


But when I met The Suit again two week later for our first proper date, he complimented me in a totally smooth way. When I took my (ridiculous vintage fur) jacket off, he said “That is a fantastic jacket.” Good, something specific that I could respond to: “Oh yeah it was a hand-me-down from my godmother, I hardly ever wear it because it’s a bit OTT but I thought if I can’t dress up for a fancy dinner date, when can I?” Not smooth. In fact, verbal diarrhoea. To which he replied, “Of course! And you do look beautiful. Would you like a drink?” Smooth.

He had booked the arm chairs next to the fire at a fancy restaurant. When I apologised for my tardy responses and thanked him for waiting two weeks to catch up, he said ‘As if I wouldn’t, you’re great!’ He seemed into me. The last three guys I’d had a semi-serious series of dates or flings with were good dudes who I connected deeply with, but for a variety of reasons it wasn’t the right time (not into monogamy, not ready for a ‘relationship’ or still not divorced), or they just weren’t into me enough to make time. The Suit seemed into me and it was intoxicating. He had that twinkly look in his eyes. You know that look? When your eyes meet and they look deep into them and holds that gaze? When their eyes seem to smile? When without speaking their eyes seem to tell you they’re really there watching and listening and that they’re kinda really into being there too? When someone, a date, a partner, a friend, a family member or a colleague, looks at you with curiosity and respect and joy? I hope y’all have had someone look at you and listen like that. It’s pretty fucken ace.

We ate dinner, which I’m normally not into on a first date, but when you’re at a fancy joint in heels and fur and mascara that feels like you accidentally painted it onto one of your eyeballs, why the fuck not? This joint was normally definitely outta my price range but I’d budgeted for it that week. I went all out and ordered the lamb. It was bloody delicious.

There were so many things I liked about this bloke. He listened well, he told a good story, he didn’t shy away from real talk, he liked me and he wanted to move to the country once he’d found a job, a dog and a woman to move with. Despite all this, a strong desire to touch his face or kiss his lips did not manifest itself. He seemed a little stuck in his life. He did not especially like talking about his work. He was not looking forward to turning 40 soon. He said something I’ve heard a few fellas say who feel older or that they’ve been single for more than they’d like to be: I’ve just learnt that the harder you try to grasp something the harder it is to hold, you just have to let go and not try so hard.

I thought two things in response to this. One: letting go? Sounds like giving up! Laaaaame! This was an affront to my entire approach to dating – which is that it’s a numbers game that you have to be in it to win it even if you do probably end up bumping into your true love serendipitously in the line at Centrelink one wintry midweek morning.

Two: I heard so much yearning in that. Almost desperation. It sounded like as much as they were trying hard to let go, either they weren’t letting go or the fact remained that they were still trying hard. Fuck, aren’t we all? Trying hard? Wasn’t I? Otherwise why the fuck did I spend so long getting dressed and daydreaming about what this date would be like even though I couldn’t actually remember what his face looked like and had a sinking feeling that I may not want to kiss it? Why, despite knowing my gut wasn’t feeling any chemistry, did I blush when he said “I think I’ve made it pretty clear I’d like to see you again”? Why did I respond, “You’re great! This was great! Let’s do it again!” even though I had just made it pretty clear our kiss goodbye on the lips would remain a Church kiss and not a pash?


Maybe the things that annoy us or repel us in other people are the things that annoy us about ourselves. I realised what it looked like when someone comes on strong. Not overly strong, but makes their intentions clear, isn’t shy about their feelings. Maybe this is what I’d been doing to those last three blokes. Coming on strong. Trying too hard. Perhaps the force of my feelings feared them a little. I thought that was honesty and integrity – but maybe you can still be real and keep a few cards to your chest. I mean, I didn’t tell them I loved them or try to move in with them or suggest names for our firstborn but maybe that kind of desperation can be sensed. Maybe you can smell it. I was so scared of men smelling that yearning emanating from me, but I also was so sick of blokes not being ready to meet me where I’m at. Here was someone who was ready to meet me. Why wasn’t I running towards that?

Maybe – a desire to be with me is not the only quality I’m looking for in a potential romantic partner – maybe it’s the baseline.

Maybe – when someone is real with you about their feelings, it’s not a turn off, it just makes you super cautious about how you respond if you’re not feeling like you’re matching the intensity or surety – lest you hurt their feelings. “I don’t want to waste your time if we’re looking for different things” – I’ve been told that in the past and now it’s how I felt towards this man.

Maybe – when you can see what a future with someone would look like so clearly that it scares you a little bit and maybe you don’t feel as ready to jump into that as you thought you were.

Maybe – I just wasn’t super turned on and that felt shallow and lame because he was such a decent bloke. The kind of good guy who ticks boxes and who your mates and mum want you to end up with. Maybe I’d never experienced the ‘slow burn’ and spent enough time with someone who I wasn’t turned on by, for long enough for the other less obvious parts of them to emerge and turn me on. Maybe I was comparing him to the babin’ hipsters I’d met at another speed dating even the night before. Maybe I was a superficial bitch and that felt a bit shit.

Maybe I was pretty tired from finishing an intense week of work back in Tassie immediately after finishing my masters and two people I knew had recently died and I was tired and wired and raw and my feelings were all over the place and I didn’t trust them.


Whatever the reason, when he texted the next day to say how he’d like to meet up but ‘totally fine if you don’t want to – you’re awesome in any event’ I jumped at the chance to exit and fired back a very complimentary goodbye text.


I still wonder if I did the right thing.



Contemplative sunrise view from my bedroom door. It’s not as beautiful as Boat Harbour, and I still feel sad and lonely and confused sometimes, but this feels like the right place to feel those feelings.



10 thoughts on “Trying too hard

  1. These are all the things I was feeling with Xander! You simply verbalized (ok, wrote!) it perfectly. I was and still am so confused by it all. He’s such a great guy but I just wasn’t feeling it and it made me feel bad.

  2. Thought provoking. Particularly enjoyed all the angles discussed through your ‘maybes.’ I find that part of that sort of connection so frustrating but inescapable, when you’re looking for an answer but can only find many theories. Great read, thank you x

    • That guy! Yeah – I should update y’all shouldn’t I? Things have been a little hectic since that all went down but thanks for the reminder and for your patience x

  3. God I love your writing. And this sooo resonates – I think you said it to me on your comment on a recent story of mine:
    “I realised what it looked like when someone comes on strong. Not overly strong, but makes their intentions clear, isn’t shy about their feelings. Maybe this is what I’d been doing to those last three blokes. Coming on strong. Trying too hard. Perhaps the force of my feelings feared them a little. I thought that was honesty and integrity – but maybe you can still be real and keep a few cards to your chest.”

    So true DD! And tbh I’m not so sure about absolutes and generalities. I have no idea whether people grow on you. All I do know is that if you’re really feeling it with someone, there’s no guarantee that they’re good for you, or it’s for the right reasons.

    Love your work, sista x

      • Oh mate, I’d be honoured – go right ahead! Yes I think I was composing this post at the same time as commenting on yours – mulling it alllll over.

        Yeah I think you’re right about absolutes/generalities, and very true point about strong feelings not being a guarantee. Maybe feelings are not to be trusted? Maybe the heart AND head need to be listened to? Which you can only really do if you’re in tune with your instinct, which perhaps I’m not at the moment.

        Anyway, I’m stoked that this is resonating and thanks for sharing your thoughts and kind words x

  4. Reblogged this on Unleashing the Cougar! and commented:
    How do we know when we’re trying too hard, or just being too…..something? How do we know when we need to back off or just chill? How do we know when we’ve found the right person, or a right person for right now?

    This is another beautifully crafted and thoughtful piece from a sista blogger on the same journey – as so many of us are, delving into the weird modern dating world to try to find connection and intimacy. She voices so well an everyday scenario and the frank self-assessment of her actions and feelings. Read on if you dare!

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