Seeking Arrangment

SugarDaddyMeet.com wasn’t working to well. Besides Oliver, all I had to choose from was a very young (in comparison to the hundreds of other 40-50 year old men), clingy Italian man and a couple of 40 married, slightly heavy men. I Googled ‘Sugar Daddy’ again and searched for a new website to sign up to, expand my search for a sugar daddy.

Seeking Arrangement caught my eye. I remember reading about it in a blog and a couple of internet reviews all recommending it. I had always thought it was an American website, but it was actually international. It was quite impressive; it was available to almost all countries around the world. The sign up was very simple at first glance, email, password and birthday. I filled those in quickly and it led me to a very long questionnaire to fill in. A part of me really didn’t want to go through another long questionnaire about myself, but most of the longer questions I had already wrote a response for SugarDaddyMeet. It didn’t actually take that long, and before I knew it, I sent my profile through for approval and uploaded the same photos I used for SugarDaddyMeet. I received instant access to the rest of the website but I wasn’t able to search. The confirmation email I received explained I needed my profile to be verified and approved before I could start searching, including two appropriate photos. Seeking Arrangement seemed more thorough, their website advertised verification of all members.


It took two days for my profile to go through. Once my profile and photos got approved the emails started pouring in again. There was ‘Papabear’ a 50 something year old ‘pappy looking for a baby’. Gross isn’t it? Then I got a wink and a ‘Hello’ email from John who gave me permission to view his private photos. He only had one photo uploaded, a cropped image of his large, hairy beer gut stomach and oddly large brown nipples. And finally, a line up of men who used very old photos of themselves. There were those who took a photo of a photo with the flash still on, and there were those who scanned their old fashion print out photos. Seeking Arrangement wasn’t offering anything different to SugarDaddyMeet, it was just a little more professional.

Among all the emails from SugarDaddyMeet and SeekingArrangement a flagged ‘important’ email popped up. It was Oliver. I had marked all his emails as important and any future emails from him would stand out.

…No .. I’ve never had a sugarbaby before. Have you ever had a sugardaddy? 
Oh right .. how much time does escorting take up? I really wouldn’t know I can say in all honesty. So sugardaddymeet was a happy compromise for you? I’m afraid you probably have got offers of financial assistance greater than mine?  

Oliver x 
PS .. here is another pic if you like! It was taken recently in Solomon Islands .. 
He didn’t explain why he hadn’t replied at his normal time but his casual reply soothed away the crazy scenarios I had pictured. It was late when I read the reply, I was relieved he had finally responded but exhausted with my side search for other sugar daddies. I took a peak at the photo he attached and almost jumped for joy. I still to this day don’t know what it was exactly that made this photo amazing, but I think it may have been the realness of the photo. A cloudy beach day, the wind passing through the trees in back and his hair. A wide eyed smile and casual beach wear. It was a little unfocused, the photo was probably taken by someone who didn’t really know how to use cameras. A very realistic photo of a very possible Sugar Daddy.


Over the course of just a day Oliver and I had exchanged a number of emails and I had already learnt so much about him and him about me.

Hi Summer

Yeah I was thinking the same thing – nice we contacted each other at the same time! 🙂

I guess I’d ask first of all what you do (study perhaps?) and where you live in Sydney? I’m at Rose Bay, so I guess I was hoping to find someone in the eastern suburbs.. ??

But I definitely agree with your approach of finding someone fun and interesting! Work is pretty busy for me these days, so would love someone friendly and easygoing I could meet up with once or twice a week and just hang out with. Hopefully someone a bit interesting! And yes, in return, I would offer an allowance.
Oliver x

I told him I was studying a Bachelor of Science full time at the University of Sydney and assured him I didn’t live to far from him. I asked about his work and what his busy schedule might look like.

Could you also expand on the allowance part?” My answers and questions were building to one topic really. I was curious how much he would want to pay for a newbie. I didn’t want to suggest an amount first just in case it was too low and I miss out on extra cash.

Hey again!

That’s cool – studying science at Sydney! 🙂  
You’re not too far away! Sounds possible anyway .. Do you live with your folks?
I work for the NSW Parliament and it can be busy work, especially when parliament sits late into the evening.

And responding to your question, I guess in an ideal world, you could come over once a week after uni (maybe Monday evenings because parliament definitely doesn’t sit late that night). I know the nature of the site – sure I’d love a partner, and in return would offer you say $300? But as you say – I would hope to genuinely get on with you as a friend too. And I’m sure I could drive you home too if you caught the bus from Sydney uni to Rose Bay.

Oliver x

I took my phone out and hit the calculator app. Oliver wasn’t very clear how long an evening would be. If it was a couple of hours I would be making a lot of money an hour. But if an evening included dinner and entertainment like a movie or a ‘long walk along the beach’, that would take about a generous 5 hours. Then I would only be making $60 an hour. However it was still a lot higher than my wage as a sales assistant and I would just get to hang out with a new friend and be paid to do so. ‘I guess for a newbie $300 is a good start.’


We continued emailing throughout the week. Oliver would normally reply towards the end of the day, around 6 or 7 in the evening. I assumed it was on the way home after work because it almost seemed it would fit into his busy schedule. I asked more about his work and eventually we got on to the topic of why we were both on the site.

‘Professional girls’ were discouraged quite strongly on the website. When signing up there was a warning advising anyone who was a professional prostitute or escort using the website to find work would face legal consequences. Even on a few profiles, men would add a small side note asking not to be contacted by these girls. So I didn’t want  to come off as one these girls and lose a great opportunity but at the same time I wasn’t like them.

There are lots of things I’d be curious to know about you. But perhaps not being too intrusive, why did you join this site? You don’t have a boyfriend at the moment?
Oliver x

Well to be honest, there are two reasons, the first being the concept of the site. It’s very intriguing and different and I like that! Second, it’s an alternative to what I was going to go into previously. No boyfriend at the moment, I haven’t met the right person yet. I know that sounds very cheesy but it’s the main reason. 

May I ask why you joined the site?
Summer Xx

Ha ha .. yes the concept of the site is a bit intriguing. Different to normal dating sites anyway! What were you going to go into previously if I can ask? An RSVP-type site?

I joined just to try something different. I joined after my last relationship ended. That was a while ago now, but now trying to give this site a proper go! 🙂

Btw – if you’d like to chat more by email, rather than here, my address is opet5892@hotmail.com
Oliver xx

How do I explain to a complete stranger I was thinking of becoming a prostitute?Honesty is usually the best policy, but stretching the truth works better sometimes. I replaced prostitute with escort and my response was already looking less seedy.


Hope i got the email address right, or else this might get awkward hahaha 

Have you ever had a ‘sugarbaby’ before? 

I was going to go into private escorting, but that required way to much time. Time that i didn’t have. Financial assistance was another reason I joined the site. Forgot to mention that before. hahaha

Summer xx


The evening came and I hadn’t received an email from Oliver like usual. I was a little worried Oliver thought the ‘escorting’ was a little too much, but it was still early and he did mention he was a busy man. My phone would go off with Facebook messages and WhatsApp notifications but no email notification. Midnight approached and I still didn’t receive anything from Oliver. I had class the next day and couldn’t afford to stay up any later.

I closed my eyes and curled up in my sheets.My brain lit up and started going through the possible scenarios that would stop Oliver from emailing me. He was just stranger but he had already made an influence on my life.