There are a handful of moments in life that make us truly analyse our past, present and future. They mostly centre around new beginnings; New Year’s Eve, the death of a monarch, and in my case, the start of my thirties.

Age isn’t something I have been conscious of until this year, as the youngest of three and someone who perpetually dates older partners – both men and women – I was always the young one in my social interactions. I’ve often thought there is little difference between myself and those older than I, yet suddenly, as I sail into undeniable adulthood, I can’t help but notice how age indeed changes us. I don’t, however think this is negative; it’s just different. For example, I now differ in romantic situations because my expectations are higher. Someone to waste three years with when I was 24 was well, exactly that, but at soon-to-be thirty, I don’t feel like wasting time. That’s not to suggest I am dying to settle down (fear not quite the opposite!), but rather those who I surround myself with must bring me value, as I hope I do to them.

Value means different things for different moments and relationships, and I count some of my clients within the remit of personal value. Someone who supports and elevates my career while giving me incredible experiences, such as the client who has booked me for extended dates every month for three years. This person has also been a sounding board in moments of uncertainty; due to the length of time we’ve known each other and spent together he is one of the only people who knows both Olivia and the real me intimately. Sure some of my friends know I am a professional companion, but they’ve never met Olivia. There are others who I have known over an extended period who have helped me discover and hone my dominant side, such as my very first pet pooch who I have now been training, humiliating and adoring for over two years.

An interesting question that comes up at the start of my new decade is “Am I where I thought I would be at this point in my life?” and I think the extreme duality of self that I inhabit means this answer must be no. That’s not because being a companion was an afterthought or a passive endeavour I have landed myself in, – I love my work and feel it suits my personality. But being a companion does mean I live a very unconventional, secret (and sometimes isolating) existence. Even though I came out as a companion, I still choose to barely mention it to those outside of the industry, meaning my adventures feel very separate. Throughout my journey, I have always had this sense of Olivia having an endpoint, as though the end is always looming, but the longer I stay, the more this sense of an ending wanes and Olivia becomes a more significant part of me. I still enjoy the thrill of separation and, on a wonderfully fun extended first date recently, my client and I talked about how secrecy and taboo are undeniably a huge part of the allure. It’s like fantasy and a deeper sense of realism rolled into one.

It could be because I am fortunate with the experiences and clients I tend to attract. I specialise in extended dates, which means I have 2-3 long dates each month. I mean 24 hours and longer by these, but they’re often two to three-night escapes. I tend to prefer these to take place in England, I don’t encourage fly me to you’s (FMTY), as for me, this would lead to quick burnout and with London, Bath, the Cotswolds, York, Edinburgh and more incredible locales on my doorstep I like to meet in the UK. I love travel dates but reserve these for at least date two. Beyond extended dates, most of my other dates are on the longer side e.g. 12-18 hours or four to ten-hour dinner dates which lead to incredible experiences. I want to make it clear that I adore and encourage lunch/brunch and dinner dates of four hours – these are usually two hours of dinner and two hours private time. Admittedly less than four hour dates do feel a little rushed and like I can’t fully get to know or explore which is why I don’t encourage them.

I am a huge music and art lover and have connected with many of my clients through these mediums; whether it’s simply listening to our all-time favourite albums together or discovering new music in many of London’s live music venues, it’s something I truly adore. Similarly, books, museums, exhibitions, and even fine wine experiences can be great way to connect and discover one another. I have written before about my hatred of mundanity and small talk and this might be why I enjoy the conversation these mediums evoke. Whether it brings up topics about the first time we saw a particular masterpiece in person, or our teenage rebellious years when we found solace in a particular album.

Duality

I have never wanted to be a full-time companion; admittedly, I like the duality of having two businesses and the safety net of two unrelated incomes. In August, I accidentally indulged a glimpse of what it would be like to be a full-time companion for the first time ever. Since launching my new site I have had more new client requests than ever before and therefore had a month worth of incredible dates. I excitedly set an ‘out of office’ response for my vanilla business and spent following days in various luxury hotels in London, Oxfordshire, The Cotswolds and Birmingham. Usually I’d have left London in between (I live outside) but I got myself a hotel in the city for my days off and enjoyed a sponsored photoshoot (photos coming soon I hope! I have not seen them yet!) from a new friend in China followed by a brunch date with him the following morning, a two-night first date complete with an appearence from his favourite (adorable) Canadian companion and a gorgeously relaxed 24-hour catch up with a client I hadn’t seen for a year. Between these I also had a delicious spa day with some fellow companions I hadn’t seen since 2019. I loved this glimmer of full-time companion life, but I also liked coming back to reality.

Even now, part of me can’t shake this feeling that my Olivia escapades aren’t real work (don’t worry I know they are! It takes a LOT of prep and effort to look, feel and be fabulous a few hours let alone an entire month straight). But I can’t shake that I need to maintain a presence in my other industry too. I have worked hard throughout my entire education to build that business and although it’s becoming my secondary business with Olivia being my priorty, I don’t want to lose the skills obtained and time I put into it. Plus my long-term goal would be to sell my vanilla business in ten years and do something completely different.

So as I look back on the last ten years, and forward to the next I am intrigued to see what it brings. In my 20’s I was always going with the flow and although open to taking risks, I was very much happy to see what happened. Now I am more of a driver in where my life and two businesses are headed.

Where do you see the next ten years of your life taking you? Perhaps we can discuss on our first or next date,

Olivia

Xx

If you’d like to send me a gift for my 30th, please consider Liberty’s, Bordelle, Selfridges, Prada, Taschen, Fortnum & Mason, Harrods (or any of the spas on my Wishlist). These can be sent to info@meetoliviasinclair.com. If you’d like to meet I am available from the WC 10th October for dates, new clients must fill out my booking form (I don’t accept date requests from people I don’t know via email as you need to agree to my booking etiquette and Terms). Existing friends can contact me via Whatsapp, email or Discord.