Secret Diary Of A Single Woman: Dating Real-Life Story - Part 1

Dating in 2014. It's hard work, people. I haven't dated since, well, 2003. I got married that year, and even before that, as a twenty-something woman, whoa… it could be tricky, frustrating, and frankly, tiring and emotionally exhausting. Mixed messages, and unreturned phone calls and dumping via phone… there were exceptional times, of course. And I am grateful for the shitty times in order to get to the good times.

I asked a friend of mine, who I know is single and fabulous, what it's like 'out there', and would she be willing to write anonymously about it all. Would she? Hell yeah. She stayed up late and wrote like mad about her secret dating life. She later told me it was incredibly cathartic for her to write it all down. My guess is that it was akin to a 'purging'… and now she is free to start a clean slate, post-'detox'.

Here she is, in her own words, her 'secret single life':

"It’s Monday of the long weekend, and I’ve had a really quiet ‘normal’ weekend. I am grateful.  My family are fine, my friends are all fine, and I am fine – and I want all of those things to stay that way for as long as possible. I am grateful for these things, very grateful.

Ultimately though, something is missing from my life and all I can think of is two things – either there is something wrong with, or I am missing a man to share my time with. To be able to give that person all the great parts of me – and he can also have the ‘not so good’ parts :)

There’s a hole deep inside me as a person, that has never been filled. Well, that’s not strictly true. I thought it was being filled, but then as quick as I thought this just might be “it” – it was no more.

I did the brave thing and stayed friends, he had decided to move on to greener pastures, and ultimately that was okay. I am who I am today, and have lived the life I have, all because of that decision he made. 

What hurt the most is, we were friends. We were intimate friends, but friendship was at the base of our connection, and I miss that friendship. I miss the flirting, and the laughter. He was the first (and only) man that had swept me off my feet. I felt like I was floating. It was long distance, so weekends were spent together. This story of love lost is not the basis for this post – but it does make a good story.

So, this warm night in Sydney I sit at my computer, and want to share what it’s like to be a 40-something woman, who has never been married, has no children, has never really don’t the whole ‘get out there and date’ thing. As a 40-something year old single, straight female, I have come full circle this year.

I can’t fill the hole inside myself with a nice meal out with friends, or a great piece of cake (believe me I tried, and 7kgs later I need to take a step back and shed those kgs – feeding my face with calories will never give me ‘satisfaction’ or ‘comfort’). 

I can’t fill the space by going to work for 10 or 12 hours a day, sitting at my desk filling my head with people’s sad stories, all because I still having an inner ache that I want to get home and find someone waiting for me, who is happy to see me, and has a hug and a funny line to throw, someone who I want to exhale with after a long, stressful day.

So, I’m rolling back 11 months to late November 2013  I had a great 2013. I had got my act together. I was feeling confident in myself, and I felt like it was time to date. It had been 11 years since I had gone out with anyone (Mr Swept-Me-Off-My-Feet).

So, I put up an online profile. I had met “Mr Swept Me Off My Feet” via a dating site, and thought I would try my luck again  I was using a different site this time, a more mainstream, well known one. 

I wrote the blurbs, and ticked all the boxes I needed to tick, and paid my 3 month membership. 

By the end of the first 2 weeks, I had a nagging feeling that maybe this was not the best idea for me. Maybe, just maybe, I should ‘work on my technique’. I had only ever been intimate with Mr Sweepy, and I started to think that maybe that was my issue – maybe I needed to improve my bedroom prowess. 

So, I will be brutally honest, and confess to looking up and researching male escorts:  how it works; what you do; what happens etc.  I considered it, but most of the male escorts were really young – I could have given birth to some of them… so that was off the table.

I really can’t do the whole bar/pick up thing – I never have been in to the bar/club scene, so that was off the table to.

After deciding I would return to the net to find a solution, I decided that what I needed was a “friend with benefits” an “FWB”.  I cannot even remember now, how I found the website I did, I must have searched for something and it popped up.  It is not a well-known website.  It is one of many affiliates (as these sites seem to be) and I became a member.  It was great, I could pay the membership by a one off payment added to my mobile phone bill – once the 15 days had run out – that was it, no auto-deduction of another membership fee.  It was on my terms.  I could pay when I wanted another hit of man-ttention and let it lapse when I didn’t.

I researched (yes, I’m a bit of a nerd) about the whole psychology of a “FWB” situation; how you’re supposed to feel, what it’s supposed to be like.  Ultimately, you can like the person, but once you develop feelings for the person, you need to come clean and fess up – because ultimately you don’t want to get hurt, nor hurt anybody else.  Be upfront, be clear, no mixed messages.  It was time for me to exercise these underused traits in my personality.  It was time to put myself out there, no holds barred.

So, I needed a profile picture.  I didn’t want to put my face on the site.  One sunny afternoon I figured “what do I have to lose” and snapped a tasteful pic of myself, slightly suggestive.  It was showing my best physical assets, with a cute floral bra, and my hand demurely resting on my décolletage.  Sexy, soft, and demure – with a hint of ‘mischief”. 

My profile was upfront and honest.  I stated that after a big 12 months of personal changes and growth, I was ready to put myself out in the dating world again and I wanted to live a little.  I had a lot of years to make up for.

I got messages straight away. I also received lots of nude photos of men’s bits (MEN: please note, some women – and probably most – don’t like shots of your bits, we would rather look at a nice chest/chin combo or a nice wrist/strong hand if you don’t want to show us your face).  The men who showed me their bits, I didn’t even bother responding to. 

The men who I did reply to, I weeded through very quickly. You can pick the crazies (and there are SOME crazies); you can pick the people lying because their stories don’t make sense; and you can uncover some really lovely men.

A site like this just “puts it out there”. You know what they want, you know what they’re into and visa versa.  90% of the men I talked to are just like me, wanting some companionship, wanting to feel close to someone.

My profile was clear, I was looking for a FWB and I was open to a long term relationship if that eventuated.  I stayed away from most of the married men who were up front in telling me they were married, and for whatever reason were on this site. 

I did get let down, and I did get lucky, and I did get a little singed around the edges – and I have a bunch of hilarious stories to share with my girlfriends over coffee and/or cocktails. 

Here is a rundown of my 10 months of ‘putting myself out there’:

Mr NZ – based in NZ, he is a lovely man, early 50s, single, and if he ever flies to Sydney and I’m free, I’m meeting up with him.  He was the first person I spoke with, and we still speak every now and then; we are just on the same wave length and our writing to each other definitely adds a little heat J

I then struck up a conversation with 2 people – a builder and a policeman.

Mr Policeman – based in Sydney, upfront, single but had grown children, mid 50s; everything going great guns, and I thought ‘that’s it, this is my FWB’.  We talked for about 4-5 weeks via text and email; I liked what he had to say, we clicked mentally and that translated to some interesting emails and texts.  We were going to meet just after NYE when he returned from a work trip. Work trip came and went; NYE came and went – and nothing at all.  He had disappeared. 

Throughout talking to Mr Policeman, Mr Builder was always a constant.  Good morning messages, checking in through the day, just a really lovely man. Very upfront, very honest, very sweet, VERY patient.  So, by February I thought – this is ridiculous – how hard is it to find a man to get intimate with, so I bit the bullet and agreed to meet Mr Builder.

We met in a public place the first time.  I was so damn nervous.  He was late, due to traffic.  We met a local cricket ground, lots of people around.  I didn’t want to meet for coffee, I just wanted to meet this guy to see whether he had crazy eyes or not.  And he didn’t.  He was shorter than I expected, and a little more portly – but I am not a stick figure by any means, and he had the loveliest blue eyes and was able to talk freely and easily – I was sold.   So we talked for a couple hours and he had to go, but not before asking if he could kiss me.  Who was I to say no – this is what I was here for!  And, it was nice.  Not earth shattering and I think I mumbled something like “I thought I forgot how to do that”.  He knew my story.  I had been with one person for a short time many years ago, I wanted to break my drought and my experience was (I thought) quite limited.  So we decided we would meet up in a more private place. 

Now, what I didn’t realise at the time, which I do now, is that IT DOES MATTER where I book a room.  I didn’t think it would, so I made a fatal mistake of booking the cheap nasty “revamped” Formula 1 local to me. I cringe as I type this.

Honestly, I felt like Goldilocks walking in to that place.  I had planned to spend the night, even if he wanted to leave in the early hours.  I had my professional looking red carry on rolly bag; I looked professional as I had checked in after work.  The foyer was awful; there were seedy dudes hanging around outside; and I felt really “ewww”.  I gave myself a talking to.  “Snap out of it, you’re a grown woman, this is what grown women do. Be confident, be poised, be the person you’ve always wanted to be”. 

So I checked in, and opened the door to the room. I texted Mr Builder straight away:  “this is the dodgiest room ever” to which he responded with an “lol” and a “don’t worry, I’ll be there in 10 then you wont notice the room”.  I still laugh as I think about it.  It’s what I needed to hear to feel at ease.  He was not a Casanova, his dry spell wasn’t as long as mine but he was in a dry spell to, so we were meeting on a mutual footing.

So visualise this, the door swings open inside the room to the right. You see on the far wall a window with a dodgy blind hooked over the windowsill on a hook; there’s a basin in the far corner with 2 towels, and as you step inside on your left is the plastic pod bathroom… it’s like ‘tupperware’ meets bathroom 101.  Moulded shower recess and a half a wall and a toilet – at least there was a door on it.

So I wheeled myself inside and put on some music and waited. I told myself “it’s not too late to back out, I have the control here” and all those other things. And truth be told, I didn’t want to back out.

Anyway, I’ll miss the bits that will make it in to my Memoirs one day, and just say, that he is a lovely man, he was very conscious of the fact that this was very much out of my normal, and we did enjoy the three or so hours together. 

I had not been clear of my expectations though; and he left after 3-4 hours. We’d talked, shared a laugh etc but he did leave and I felt very ‘empty’.  It’s not what I expected to feel.  He was  very polite in asking whether I’d like him to wait and he’d walk me to my car, but I said no, he should go, I’ll just get ready and go myself.  And he did. 

It was great for my self-confidence; it was great for me as a woman in total control of her life – but, I felt empty and deflated.  I got myself hauled together, looking just as professional as I did on the way in, and I checked out.  I felt very seedy checking out, and silly me didn’t realise, this happens at that place all the time – so there’s actually a slot you just slip your room card in to, and that’s you checking out – no one bats an eyelid. 

I know that now after telling the clerk at the desk the only lie I could come up with on the spur of the moment.  “I need to check out, change of plans, I need to get to Canberra for a meeting at 7am. Have a good night”.  I’m sure he thought “yeah right” but I’ll never go back there again so I don’t care!

What I didn’t realise, was that would be the only evening Mr Builder and I would see each other.  We had discussed, and he had decided to take a job on the North Coast for 12 months. I told him it’s too good an opportunity to miss out on, take it.

Stay tuned for PART TWO of this piece.