Chapter Eleven: Emily


It takes a lot of guts to ask a girl out. Guys often forget this until the time comes to actually ask and suddenly the reason why this is so hard suddenly becomes apparent.

When this moment happens you have two options: you can the ignore the part of you that is shaking in fear at the prospect of rejection and just ask, or you can bail completely.

Confident guys, those guys that seem to be able to get every girl they ever want, I’m certain never EVER feel any sense of doubt when asking out a girl.

My advice: Do not ever bail completely. Ignore the fear and the doubt and just ask.

If you don’t, years later, even if you’re entirely gotten over the girl you’ll still kick yourself for not having not spoken up when you did.

Exhibit A.

When I worked at the law firm I used to have to go into the same bank branch multiple times during a day. This particular bank housed the law firm’s accounts and as such we did all our banking through them.

As I was constantly going to this bank, I got to know the many staff members that worked there. I became friends with them.

After about a year Emily got transferred to the branch. As with every newbie, I got to know her, but with Emily I felt a familiar stirring of emotions. She was attractive, she was nice, we got along, we play fought and mocked each other. It was grand.

I had worked at the law firm for about a year and had long since abandoned the prospect of anything ever happening with Abigail. Part of me was stubbornly refusing to let go of the feelings for Abigail, but deep down I knew nothing was ever going to happen.

Then one day Emily mentioned her boyfriend. I pushed aside all feelings that were beginning to form for her and focused purely on the friendship. It worked well, surprisingly well.

In the week following christmas neither the bank nor the law firm were closed but both were quiet. My consisted of deliveries for the lawyers I worked for, and not only were there no lawyers were working that week, but a lot of offices were closed.

I constantly found myself bored out of my mind in the office because there was literally NOTHING TO DO! So I used to escape to the bank and talk with tellers, and the friendships with the tellers increased.

Then, I remember it being just before Easter, Emily threw me a curve ball.

I walked into the bank one afternoon, it was quiet and there was no line. I wandered up to Emily’s window and placed the cheques I had to deposit for the law firm down.

Do you know much about any of the Gophers for the other law firms?” She asked. She had a playful expression on her face, this was obviously building up to something.

Some more than others, why?”

How much do you know about Trent?”

Trent. Nice guy, he worked for another law firm in our building. We got along, but didn’t know each other all that well. In my head he was like the law firm version of Liam Early. One of those people born with natural charisma who you loved to hate, but couldn’t because he was such a nice guy.

But why was Emily asking about him? She had a boyfriend didn’t she?


I froze for a moment. A grin creeping across my face.

You like him don’t you?” I asked playfully.

She told me she did, she didn’t deny the fact at all. In fact, all her co-workers knew about it as well.

Don’t you have a boyfriend?”

She didn’t. Not anymore. They’d recently broken up.

Being a good friend, I told her I’d find out what I could. Walking out of the bank a small battle started waging in my head that would continue for the next few days.

Now is the point where I mention that just the day before Emily had given her notice as she’d landed another job.

Two conflicting frames of mind instantaneously appeared in my mind. If they’d had a conversation it would’ve gone like this:

She’s single.”

She’s a friend.”

She likes Trent.”

Be a good friend, find out whether Trent’s single and tell her.”

What if we could be more than friends?”




I could tell her Trent’s got a girlfriend. That would take care of the Trent situation!”

And if you don’t have a chance with her, then you’re really willing to screw up Trent’s chances?”

This little mental war continued on for a few days, until I finally resigned myself to do the honourable thing and find out if Trent was in fact single or not.

Silently hoping that he was in a happy, committed relationship I asked a mutual friend for the run down on Trent’s love life.

He was single. Bastard.

Emily took the news exactly as I thought she would. She invited Trent to her farewell party, which was actually a week before her last day.

I showed up, he didn’t. Part of me quietly hoped that this meant he wasn’t interested.

I was flooded with guilt when I saw how disappointed Emily was that he didn’t show. He would obviously make her happy, and I was….well…..a friend.

A week later Emily’s last day came. Since it might have been one of the last times I saw her, I’d made a firm decision to ask her out that afternoon.

I had lunch with friends from work to celebrate someone’s birthday. I seized the opportunity to try and use alcohol to create some liquid confidence. It didn’t work. All it resulted was my inability to walk in a straight line and strange difficulty in doing my afternoon deliveries.

My last trip to the bank came.

She was standing by the door. I walked up and said my goodbyes, my stomach filling with butterflies.

Just ask her out. ASK HER OUT NOW!

I didn’t.

Depressed and angry at myself for bailing I walked back to the law firm and sat down at my desk. Staring at a piece of paper that had Emily’s email address on it, which was nestled on a computer with access to the internet.

When you’re standing in front of a girl that you’re about to ask out, just open your mouth and do it. Because if you don’t, you’re bound to do something you regret later on.

I didn’t have any contact details for her. The only thing I had was her email address. From that moment on, my only possible point of contact would be her email address. It’s easy to say in an email what you couldn’t say in person. I typed, read it, erased it, typed it again, read it, and then finally decided it was okay and hit send.

It quickly became apparent that I didn’t know how often Emily checked her email address. Which ultimately lead to me realising if she didn’t immediately reply I would have no knowledge whatsoever if she had in fact received my email.

And so began the waiting period. As it was the Easter weekend I found myself with all of Easter to think it over, and of course check my email at every available opportunity. Which I did, without fail.

By Sunday evening itself, I would variate between finding a distraction to stop me thinking about, to thinking about it constantly. So much so that this entry was scrolled in my journal:


A long time ago there was a young, devilishly good looking, handsome man, who was doomed to spend all of his eternity as “boy-next-door-sexless-shoulder-cry-on” and while he built a huge castle and killed many ogres in the land (except for the ones that were his friends) He impressed none of the princess, or village girls, or maidens, or even any ugly step sisters.

Pissed at this turn of events the young man offered his soul to the devil, but unfortunately however, the devil decided he didn’t like the man either, gave him a wedgie and ran away.

And that’s the end of the story. Now bugger off, all you princes and fair maidens and the like, to your homes with your significant others.

I had a blind hope that as soon as Emily got the opportunity to read her email she would respond immediately. This at least allowed the possibility that her response wouldn’t be negative. As days became weeks it began to dawn on me that it was more than likely she had in fact read the email and just wasn’t responding because the response wasn’t exactly desirable.

I could have left well enough alone, and assumed she’d read it and her lack of response was essentially an answer in itself. I could have done this, but then I never would have known whether she had actually read it or not.

Unfortunately my blind optimism eventually worked against me. Shortly after realising that I had no knowledge that Emily had read her email or not, I started encouraging Emma, another girl whom Emily was friends with, to tell Emily to check her email.

I mentioned this a couple of times, especially after Emma mentioned she had seen Emily and forgot to tell her. I now felt the need to occasionally remind Emma about it.

Sure enough checking my email at every opportunity eventually failed, and I found myself checking frequently more out of habit than anything else. Apparently the phrase “a watched pot never boils” rings true.

There wasn’t anything special about this particular day. I vaguely remember being late to get to lunch because one of my deliveries had taken a little longer than expected.

Lunch in hand I sat down in front of my computer and checked my personal email – and was surprised to see an email from Emily waiting for me.

While I can actually remember, word for word, what the email said, I won’t reprint it here. As I’ve already mentioned, there are some things better left private, and besides no man ever wants someone else to witness him being turned down by a girl.

But man, the rejection was savage. Possibly one of the most savage rejections I’ve received to date.

Long after the fact I realised it didn’t have to be. She’d opened the admittedly harsh response by saying she was dating Trent now. She could have calmly left it at that. Once again, I won’t say exactly what she wrote but suffice to say… she didn’t. This was a rejection would haunt me for years to come.

One line in particular, which I will share, referenced me “liking any girl that so much as smiled at him” which now distanced from the situation I can say isn’t true but at the time it seemed to taint memories of previous girls from my past.

Wasn’t Danielle’s smile that shining moment of hope in a bad time? Wasn’t my first memory of Kari smiling at me in the Eighth Grade locker bay? Wasn’t Camille’s simply being nice to me was what lead to my feelings for her?

Rejection sucked. It sucked for a good week, maybe more, but in time the wound slowly healed, though that one line would continue to stick in my mind for a long, long time afterward.

I bumped into Emily months later and while the instinct was to avoid her and write her off completely, I made tentative steps toward at least some kind of friendship with her.

There was awkwardness, because there would always be some level of awkwardness, and we sent each other the occasional email, but in time we fell out of contact – as you often do with people you aren’t that close to.

With Abigail now firmly not wanting to be involved, my mini melt down passed and my faith in humanity restored by the re-appearance of the homeless guy, I was filled with confidence when I started tracking down Emily. Which was good, because I had a strong suspicion she was going to be hard to win over.

Looking back to my last victory, Danielle, and taking into account I contacted her via facebook, I figured it would be a good place to start and Emily would react a lot better to a facebook message than to a phone call from a guy whom she turned down for a date many years ago.

Sure enough, I found Emily with one search and I sent her a facebook message, and hoped for the best.

From: Liam Smith

To: Emily

Hey Emily,

You may not remember me, it’s Liam! I used to work at the law firm and was in the bank all the time while you worked there.

Okay, so this is going to sound weird but here goes: I’m actually writing a book about tracking down and interviewing every girl I’ve ever had a crush on. I started with the first girl I had a crush on and worked my way chronologically forward from there, five months & ten crushes later, which brings me to you.

I’d like to interview you for the book. I realize how crazy all of this sounds and will completely understand if you don’t want to.

If you want I can email you what I’ve written of the book so far.

If you could let me know either way that would be great.

Hope all is well.


I sent the message, crossed my fingers, and waited. It only took two hours to get a response, which looking back was a first for a girl I was contacting via the internet.

To: Liam Smith

From: Emily

Hey…pretty random! How u goin? Although this all sounds a bit strange….u can ask me some stuff! Tell me more about it?….
Talk soon

Now THIS was more like it. This was a positive response, not completely positive, but she was willing to give it a shot if I could win her over. And so I began, what I believed to be, my highly impressive message saying all the merits of the book and how it was all in good fun and no harm was meant by it. I’d done this many times by now had become quite good at it.

Normally, because you’ve heard so many times by now, I wouldn’t reprint the facebook message here, but in it I proceeded to make a fatal spelling error I wouldn’t notice till two days later. See if you can spot it.

To: Emily

From: Liam Smith

I got the idea one day at work when a girl sitting next to me revealed that she went to the same high school as me but was a few years below. Then she told me she had the biggest crush on a guy in my year and described him as being “So hot. Like a teenage Justin Timberlake.”
This blew me away, cause I was friends with the guy she was talking about, and the way she described him was completely different to how I would.

Then I got to thinking about all the girls I’ve had a crush on. Wondering what they were doing with themselves these days, wondering what they thought of me then, what they’re up to now, who they’re seeing whether they have a crush that they always think of as “the one that got away”. That sort of thing.
Then I figured it would be fun and interesting finding out the answers to all these things, and writing a book about the entire adventure.

It’s been random. I went to Melbourne and interviewed the first guy I ever had a crush on (I was six years old), I got back in touch with my best friend from year five, I even ended up organizing a year six reunion.

Nothing sells the product like the product itself though, if you want I can email you what I’ve written so far. (all 40,000ish words of it)

Like I said, it’s all light hearted and in good fun. Though, I know how strange it all sounds, and can completely understand why some previous crushes have been a little “weirded out” when I’ve contacted them about it.

Tell me what you think.

Now I’ve gotten all that out of the way, how’ve you been? What’re you up to these days?


Did you see the spelling error? Well I didn’t either. Someone else had to point it out to me. Emily didn’t respond immediately, but after fairly positive first response, I was proud of myself for at least making a worthy attempt to try and win her over to the whole book concept. I was so proud, that two days later when Sare was over I showed her the facebook message, she read what Emily had written, and then she read it what I’d written. And she began to laugh, she began to laugh a lot, she stopped laughing long enough to point at the screen at the exact point at which I’d made a fairly impressive spelling misake, I’ll reprint here for prosperity:

It’s been random. I went to Melbourne and interviewed the first guy I ever had a crush on (I was six years old)

For a moment the entire world seemed to come to a complete stop. I had just OUTED myself to the a girl I’d once had a crush. Which is all good and well if I WERE actually GAY. My housemate Phil heard Sare’s reaction, heard my whimper, and came into read what all the fuss was about. Upon doing so, he too found it very amusing, as did my other housemates when they came home.

Surely there were enough references earlier on in the message to communicate the fact that I am straight? I mean I’d said it was a book about “tracking down and interviewing every girl I’ve ever had a crush on”. But then I used those damn brackets when I referred the first GUY I ever had a crush on. The brackets seemed to vaguely imply that once, when I was six, I’d had a crush on a guy.

Before I could type a message to clear up the matter, she’d already responded:

To: Liam Smith

From: Emily

Fair enough! Im happy to answer stuff…i just wont if I dont want to!!! Im just at uni nearly finished…banking and finance surprisingly! Sorry so short…bit busy!

Well, the good part was she was willing to be interviewed for the book. Now to clear up my earlier spelling error and organise a time and a place to meet. That’s if she was willing to meet in person, at this stage, after Abigail, I was willing to accept any form of an interview.

To: Emily

From: Liam Smith


And you’re about get a laugh out of this – scroll back and read my entire spiel I just wrote, specifically the line “I went to Melbourne and interviewed the first guy I ever had a crush on” that was meant to be GIRL. Interview the first GIRL I ever had a crush on. My best friend is currently sitting next to me laughing and making jokes. I’m never going to hear the end of this one.

ANYWAY, now I’ve made a complete arse of myself – don’t suppose you want to do the interview in person? If not that’s okay, facebook’s fine, I just think better on my feet in person, and I can buy you a coffee for your trouble.

But, like I said, if not that’s okay too.

Nearly finished uni? Whoa. I can remember you telling me when you were starting. Where are you working these days?

And so it was done, I’d cleared up my sexual orientation. I was relieved.

You know, because you’ve deliberately gone out of your way to prove you’re not gay, she might take that as a sign that you are,” Sare pointed out, evilly. She was having way too much fun with this.

Or maybe,” said Stu, who’d arrived home by then and taken great amusement in my spelling being the end of me, “Maybe she’ll think that you’re pointing out you’re straight ’cause you intend to sleep with her.”

Though I’ll never admit to their faces, they both had valid points. But I was determined to stay positive. Besides, Stu had also been one of the many people who claimed I killed the homeless guy.

You’re wrong,” I told them defiantly. I then tried valiantly to think up an argument against it. Really though, I had only thought as far as telling them they were wrong, without anything to back it up. So I just left it at that.

A day later it turned out they were ACTUALLY wrong. Who would have thought?

To: Liam Smith

From: Emily

Yeah i knew u meant a girl cos it didnt make sense! Dont worry bout it! I suppose I could do it in person…when though? Im just working at Bras N Things in the Mall and also at a doctors surgery in Canberra House! Where’s ur work?

VICTORY! I flicked on my favourite song and did a little dance around the house. It was beautiful, just beautiful. She was going to be in the book, she willing to be interviewed in person, she worked on one side of town, I worked on the other. Hmmm….. that could be a problem. Nothing that couldn’t be solved however, I was unstoppable.

I sent her a message telling her where I worked, and suggested meeting at the coffee shop where I’d met the other crushes. I actually had to wait for a response here, two weeks to be precise, and just as the doubt was beginning to form that she may not actually be as keen to take part as I’d originally caught, all faith was restored with one simple message.

To: Liam Smith

From: Emily

hey sorry for late reply… my internet is not working properly and i been so busy over the uni break..workin every day…not used to that. Would it be easier to do this over facebook? Did u still want to?

Of course I wanted to! I sent her a facebook message asking for email address so I could email the questions through. I know at the beginning I’d said I’d prefer to do all the interviews in person, I also know that beggars can’t be choosers. Especially as I’d originally thought I had zero chance of getting even email interview from her.

I sent her an email with the questions, to which she responded to a few days later. As she responded to my email with both the questions and the answers I’ll put hers here:

To: Liam Smith

From: Emily

The first question, and possibly one of the only questions I consistently to remember to ask is if you ever knew I had a crush on you? No I didnt!

Since I’m going to work on the theory that you eventually figured out I did when I sorta asked you out (and my ego won’t be bruised if you don’t remember that) then the next question of “Did you ever have a crush on me?” is pretty much redundant, but what the hell, I’ll ask it anyway! So, did you ever have a crush on me? No

Now that’s out of the way, can you remember your first crush? How old were you at the time?(This is the point where I remind you it’s okay if you don’t want to answer a question) Yes Kindergarten, so 4 years old

Do you have a crush that you think of as “the one that got away”? No dont think so, i dont think like that.

Is there someone you had a crush on for a while, and then actually got together with them? Yes a few times but didnt turn out 2 be what i expected.

Was there every someone you had crush on, and then realised later on that they were the complete opposite of what you thought? Yes

And finally, just how nuts did it seem when I first contacted you? A little bit nuts! but u can do what u want!

Her answers were short, but that’s okay, she’d apologised for that. I read over her response and one caught my attention, one that stood out and peaked my curiosity.

Is there someone you had a crush on for a while, and then actually got together with them? Yes a few times but didnt turn out 2 be what i expected.

Sorry so short.

Could it be Trent? The guy who’d won her over when I’d hoped to win her over instead, the guy who…. for lack of a better descriptive term, she’d chosen over me? I had to ask. I owed to my younger self to ask. I just had to know, if she didn’t want to tell me, so be it. So I sent her another email:

To: Emily

From: Liam Smith

no probs, there is one question I gotta ask…

>>Is there someone you had a crush on for a while, and then actually got together with them? Yes a few times but didnt turn out 2 be what i expected.<<

was one of those trent?


I would have understood if she didn’t want to respond. I would have understood because really – it’s a fairly personal question, and here I was asking her to bad mouth an ex. So I would’ve understood completely if she HADN’T answered my question. But she did, and let me tell you, the response was something sweet. Writing the entire book was worth it for this one single moment.

To: Liam Smith

From: Emily

Yeah I suppose, but I’ve grown up a lot since then and I dont have crushes anymore, I’m more realistic than that and people don’t really work like that anymore either.

But yeah Trent was a loser! Well I shouldnt be that harsh, he was very simple and small minded. Like i don’t waste my time with people i just know are not the ‘one’…im nearly 25! Well I waste time but I don’t develop feelings…although THEY do sometimes…

This book could turn into so much more.. .like relationships in general in different age groups….I’ve gone thru so much since then…I feel like giving advice to younger girls!!! how do u come 2 write a book? sorry bit side tracked….bak 2 work now!

I laughed. It was a triumphant laugh, it was a laugh of relief. Back then, when I asked her out, when I worked at the law firm, when she’d chosen Trent. Well, when that happens part of you always wishes that the guy she chose turns out to be a loser. It’s very rare that years later you find out you were right.

That day I drove home humming to myself. When I got home I cracked open a beer and slunk onto the couch with my feet up on the coffee table, all the while grinning a stupid grin. Then to the empty room I raised a toast to the me who’d asked out Emily years ago, then to Emily herself, and to Trent.

I felt like a winner.

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