I’ve always been one for mulling things over with a coffee, even when nothing is happening in my personal life. So now that Emily had given me something that genuinely required thinking about, I knew I’d better book in a serious session of sipping hot drinks. My list of coffee companions isn’t long. When it was about women – and it usually was, unless I was complaining about Phil – I made my friends so sick of my passivity that they offered to ring up my target themselves to ask her out for me. After a few drinks one night at the pub, one of my friends actually followed through on the threat. She misinterpreted and, well, I’m going to be his groomsman next year. Thanks, Fitzy.

Nige’s isn’t my first-choice shoulder to cry on, since his solutions always involve dodgy pubs, dodgier liquor and palming off some girl he’d tired of onto me. At times, when he’d found me particularly exasperating, he’d offered to rent me a hooker so I could bloody well get my end away for a change and stop taking myself so damn seriously. He was certainly generous. To a fault.

Besides, he wouldn’t have seen anything wrong with the Emily escapade, and would have mocked me mercilessly for having had scruples. And so my regular need for a good heart-to-heart whinge was best fulfilled by Zoë.

At the time she was my only close female friend, which is an indictment on me, of course. I generally find it tough to just hang out with girls when I’m single because I’m always terrified they’ll think I’m hitting on them – cultivating a friendship so I can clumsily and unwelcomely shift gears to asking them out. Little do they know I wouldn’t dare. My patented approach to seduction involves sitting back and hoping the girl will realise I’m interested and make the first move. It doesn’t recommend itself through results.

That whole issue wasn’t a problem with Zo, though, because while she’s certainly attractive, we had the perfect basis for a strong, indisputably platonic friendship – a drunken pash on first-year law camp. When we had the mandatory painful conversation the following day and discovered that neither of us wanted it to go anywhere, the mutual relief – along with a shared taste for self-deprecating jokes about the incident – was enough to turn us into instant friends. Apparently we were right about the having lots in common and enjoying hanging out together bit, and wrong about the wanting to stick our tongues down each other’s throats bit. But as Meat Loaf so insightfully observed, two out of three ain’t bad.

Since discovering that the romantic road was a cul-de-sac, our friendship had blossomed. Guys often asked me how I could put up with it – right after they’d asked whether she was available and been disappointed. Zoë was very much taken in those days, so I always explained that while of course I knew abstractly that she was attractive, we were friends.

There was quite a bit to be immune to, if I’m honest. She has a petite, pale body, dark hair cut in a bob and high cheekbones – a hint of Audrey Hepburn, particularly given her similarly intense, dark eyes. Sometimes they sparkle with a lively wit and sheer overabundance of brains, but on occasion they crackle with genuine fire.

Her default mode is playful, but the intensity of her manner sometimes proves devastating for the male of the species. She focuses so intently on every conversation that guys are convinced she finds them fascinating. They start to delude themselves that there is something special there, or even that she’s coming onto them. Invariably she isn’t; she’s just really invigorated by meeting people. I was often reminded that I’d made the same mistake when I’d met her.

The other thing that put Zoë completely off the agenda was that her boyfriend Josh is an old school mate of mine – in fact, they met at my twenty-first. Since they were one of those rare couples who didn’t make outsiders feel like a vestigial limb, the three of us spent a lot of time together. Josh and I had never been all that so close, but I often joked that since I’d brought them together, it was only fair that I get the best man gig.

Zo’s response was that I had to be her maid of honour instead – one of her little witticisms about my lack of manliness. I always replied that as long as it didn’t involve a dress or in any way render me unavailable for some primo bridesmaid-scoring opportunities, I was there. To which she replied she knew I was there, but there was still no way I was scoring with the bridesmaids.

People often assumed that a friendship like ours couldn’t be completely platonic. And since I was the single one, I got accused of holding a candle. My reply was always that sure, she was attractive, but after we’d kissed, I’d been the first to say I didn’t think it was going anywhere. And that generally put an end to the ribbing.

Zoë showed up shortly after I did, only slightly grumpy about being dragged away from bed and boyfriend. She’d quickly thrown on some jeans and, judging by the Asian beer logo, one of Josh’s T-shirts. Her eyes were hidden underneath a voluminous pair of sunglasses. Not a skerrick of makeup, but then she doesn’t wear much anyway. Even so underdressed, she looked a whole lot better than I did, clad in last night’s stinky semi-formal clothes.

We usually met at Bill & Toni’s in Darlinghurst’s Little Italy. It’s only a short stumble away from her terrace, and conveniently near where I’d dumped my car the night before. The décor is so ugly it’s charming – exposed red brick, shabby grey tiles, wood-veneer Laminex tables and vinyl chairs whose plastic backs have been misguidedly moulded into a cane pattern. No one would dream of designing it like that now, but it’d break everyone’s heart if they renovated so much as one shabby tile, or added anything more to their menu than foccacia, gelato and coffee strong enough to keep even my struggling eyes open.

Zoë invariably tried to speak Italian with Marco, the barista, and it annoyed me every time. ‘Ciao Marco, come stai?’ she’d ask. He’d unleash a stream of rapid Italian she couldn’t understand. She’d laugh, nod and say ‘Molto bene, grazie.’ It was their little joke.

I usually threatened to ask Marco the Italian phrase for ‘show-off’, but never dared. This was because he never let us pay for our coffees, unless I was foolish enough to go there without Zo. Marco’s another one, I think, who misinterpreted her friendliness as flirtatiousness. I always told her she should start wearing a wedding ring just to save me time on the clarifications.

After I filled her in, she made an effort not to laugh at me, but not much of one. Evidently my little melodrama was absolutely the funniest story Zoë had ever heard, or so she kept telling me in the rare moments she wasn’t too busy giggling to actually speak. I’m not sure whether she was more entertained by the actual details, or my humiliation in the retelling.

‘I hate to ask, but could you run me through the whole Kylie thing again?’

‘You know what? I think once was embarrassing enough.’

‘Oh please? I really need to hear it again. I’m still deciding whether it’s more tragic that you tried to get her into bed by promising her a backstage pass to the Kylie tour, or that she subsequently turned out to be the president of the fan club.’

‘That’s Klub with a K, I’ll have you know.’

‘See, Paul? Now you’re enjoying it too. We both know that in a week, you’ll be dining out on this story.’

‘Really, I won’t.’

She grinned wickedly. ‘Yeah, you will. At the McDonald’s Playland where all the pre-school girls hang out.’

‘Hey! That’s a bit below the –’

‘Nappy?’

‘C’mon, gimme a break, she’s over the age of consent by at least three whole years.’

‘OK, OK; I know you’re a bit frazzled, but c’mon – this happens so rarely that I want to enjoy it.’

‘Fine, but once you’ve stopped revelling in my embarrassment, you might like to tell me what I should actually do.’

Realising I’d had enough, she switched gears into her more familiar wise-counsel mode before she cost herself a hypothetical maid of honour, and flipped up her sunglasses to look piercingly into my eyes. ‘See, this is where I thought you’d go wrong.’ She waggled a finger. ‘You don’t have to do anything.’

‘How’s that going to work?’

‘See, this isn’t actually a crisis, Paul. It’s normal. It’s what people do.’

I snorted.

‘Not you, babe, sure,’ she said. ‘But regular people.’

‘Like Phil.’

‘Ah, come on. Phil doesn’t have a monopoly on being a ladies’ man, you know. Even at MobyDisc nowadays, apparently …’

‘Well, it just seems sleazy.’

‘No, Phil’s approach is sleazy. Look, if Emily had recently gotten divorced or become a grandmother, you’d be like Phil. But all you are is a single guy, going out and having a good time with a single girl, right? And I use the term “girl” quite specifically.’

‘I know, I feel awful –’

‘Yeah, evidently; but you shouldn’t. God, lighten up about it! That’s the only problem here – how you’re feeling, not the situation itself. Personally, I’m relieved you’re finally getting out there.’

‘But what about Felicity? She’s far more my type, and I blew it.’

Zoë winced a little. ‘She’s far more your age, by the sound of things, but type I’m not so sure about. Do you really want to be dating a corporate lawyer? Or at least a corporate lawyer who’s totally into it?’

‘Well, she’d probably get the logo tattooed on her wrist if the right partner asked her. But I feel like we’ve got a real rapport, and that hasn’t happened for ages, as you well know.’

‘That’s true. I’m still in shock. You’ve exceeded your yearly average for both crushes and random shags within one 24-hour period. You’d better let me know if this is going to continue, because I’m going to have a bit of adjusting to do.’

‘Felicity’s got a great sense of humour, she’s gorgeous, and she seems to like me, at least to some degree. Maybe slightly out of my league, but I can really see the two of us together, honestly.’

‘Fine, well I’m willing to take your word for it, in lieu of other evidence. I’m not sure the Emily thing was necessarily an error, though. Perhaps you’ll have made this Felicity jealous? That might work in your favour …’

‘Oh, come on.’

‘No really. You said she’d been single for a while, right? And it’s pretty clear you showed Emily a – how can I put this – somewhat better time than she had herself. This new alpha male thing of yours is very alluring. Hey, I kind of find you more intriguing myself.’

I blushed, and was quick to cut her off. ‘I’d have thought that after all these coffees, we didn’t have much left in the way of intrigue.’

‘You certainly don’t. But really, some girl’s gonna find a lot to like about you someday Paul, trust me. You’ve just had bad luck.’

I couldn’t help but smile sheepishly and look downward. Coming from a woman who knew me so well, it meant a lot.

‘I hope you’re right about Felicity, Zo,’ I continued after a moment. ‘Maybe she’ll decide she picked the wrong guy? I’ve got to tell you, that Harris character really is something.’

‘You should have been more confident, Paulie. I always tell you: beautiful girls do it tough. Nice guys like you never approach them. They’re too intimidated.’

‘That sounds like me – the intimidated bit, anyway.’

‘I’ve met a million Harrises. Look, if a guy’s good at picking up girls, if he enjoys it, he’ll want to keep on doing it. And he often won’t value the one he’s got because it all came so easily. You know, thrill of the chase and all that.’

She sat back and folded her arms, having convinced herself, and grinned at me.

‘Whereas for you, the whole process is sheer torture, and you’re so relieved when you actually get anything happening that you treat the poor girl well, right?’

‘Out of terror she’ll find someone better and bugger off, yeah.’

‘Exactly. And I’d hate to change that about you Paul, it’s part of what makes you a good guy.’

‘Aww …’

‘No, really.’ She smiled, and I felt I might have a chance with Felicity, if she could only come to see me in a similar light.

‘But while you’re working on that – and I suspect progress will be slow – you may as well keep chasing Emily, if you like her enough. Maybe even some other girls, now that you’re such a ladykiller. It’ll do you good.’

‘Do you think my current state can in any way be described as “good”? I’ve been a wreck all day.’

She laughed at me again. ‘Not entirely, Paul. As big a wuss as we know you can be, you’re still a guy. You’ve been swaggering a little bit this whole time, pleased by what a stud you are.’

‘OK, so I’m a tiny bit glad to finally be back in the game. I admit it.’

‘And I’m sure all the girls here are terribly impressed. Hey, that one over there’s right in your demographic too.’ She pointed to a baby in a stroller.

‘Thanks Zo, that’s real sweet.’

‘Ah, come on, you’re not cut up about all this at all, are you? You just got me down here so you could boast, didn’t you? Ohhh, Zoë, I’m so confused, too many babes … and some of them are literally babes …’

I blushed again, and felt dismayed. It had occurred to me that she might be somewhat impressed by my new-found prowess.

‘Oh come on, enough with the whole crestfallen thing. All right, I’ve listened to you crapping on for twenty minutes about something I refuse to agree is even a problem, so now it’s time for me to bore you with the trivial details of my life.’

And so she proceeded to fill me in on the goings-on at the law faculty where she’d been working since we finished uni. She had seamlessly moved to the other side of the lecture theatre while finishing a Ph.D, like the academic superstar she’s always been.

I always enjoyed hearing gossip about the nutcases we had as lecturers. By the time she’d finished telling me about the contracts lecturer who’d hated me in second year getting a nose-hairball and spraying Earl Grey tea all over himself, I had completely forgotten about my predicament. Which was undoubtedly the point.