Date Thirty – The Hollywood Actor

So when I planned the final leg of this Challenge, I knew I was also planning my 30th birthday, and where I would spend the final days of my twenties.

Los Angeles seemed like the perfect destination.

At several points this Challenge has felt like a real-life Hollywood romcom, so in a lot of ways LA was the perfect setting for the final date.  Add to that, it’s one of my favourite cities in the world, and somewhere I’ve always hoped to live, and the fact that three good friends – The Producer, The Actress and The Ex-Pro – all live here, and I had my birthday holiday destination sorted!

Realising how far I would be coming for Date Number 30, I decided to stop-over in New York for a few days – fitting in Date Number 29 with The New Yorker with the process.


I considered various locations for a date – including my first Baseball game – however I wanted my thirtieth date to be on my very last day as a twenty-something.  I’ve had to very carefully plan the final few weeks of my Challenge – rather than making sure I fitted enough dates in (something I worried about earlier during the thirty), time-management became a new problem as I approached the final dates.  It was obviously easier to arrange dates in the UK than over in the US, and so I decided to make it to twenty-eight dates before I left for New York – leaving me time for just two dates in America, one in New York, and one in Los Angeles.

And so now, with just a few hours left of my twenties (and when I am technically already thirty across The Pond!) I find myself writing up the final date of this Challenge!  (And don’t worry, it was finished by 2pm LA time, so 10pm UK time …. so all done before I turned 30 either side of the globe!)


The Hollywood Actor is a friend of The Producer and The Actress, he worked on a show which The Producer wrote and directed, and which The Actress starred in (see below for the first episode!) and they have stayed in touch ever since.

When I first discussed finishing the Challenge in LA, the Producer and the Actress asked me what I wanted to do on the date, and I suggested either a baseball game (which we did on Friday night) or hiking up to the Hollywood sign.

I’ve mentioned before that ‘Friends with Benefits’ is one of my favourite chick flicks (in fact my ringtone is ‘Closing Time’, a key tune throughout the film, and the song which was playing as I sat panicking a few weeks ago, wondering whether I ought to answer the phone during The Return of The Henley Boy!)

There is a brilliant scene in the movie where Justin Timberlake and Mila Kunis break into the Hollywood sign, and he ends up having to be airlifted off it by the police.  So whilst I wasn’t planning on finishing my 30 Dates Challenge by getting arrested at the famous Hollywood sign, I did think it would be pretty cool to trek up to the sign and at least partially mimic my favourite movie.


The Hollywood Actor may not have been Justin Timberlake, but he is a RADA-trained actor who had studied at NYU.  I liked him before I’d even met him, when the Producer explained that his reaction to hearing about the Challenge and the blog was to say ‘ Of course I’ll do it! – When in my life will I ever be asked to do something like this again?!’  

Of all the dates I’ve been on, this one definitely started off in the most amusing fashion.  As a child who grew up watching teenage American dramas, there was something rather poetic about the parent-like way the Producer and The Actress arranged Date 30.  My American ‘Mom and Dad’ took control of all communication with The Hollywood Actor (as it was easier over their American cell phones), and even Googled the addresses of where we were going for him!  The night before they sent him a reminder about the date, and when he came to their flat to collect me this morning (10am – the earliest start to a date, and the first time I’ve ever been collected ‘from home’!), The Hollywood Actor even dutifully promised to bring me back safe!

We drove to the foot of the Hollywood hills, a beautiful area of Los Angeles, where the steep brown hills are decorated with a diverse mix of different unique houses which stare out over the city.

We wound our way up the hillside until we found a parking space, and then began our hike up to the iconic image of Hollywood.  The first thing we did was get lost!  Ironically, we almost went the right way, only to get the wrong directions from a fellow tourist!  We missed a gate which would have led us straight onto the well-walked tourist path, and instead ended up climbing up a steep dirt bank, having to use roots and rocks to pull ourselves up.  A police helicopter flew overhead, and we laughed about getting arrested – for a second I genuinely thought I was about to live out more of the Friends with Benefits Hollywood sign scene than I’d bargained for!

Having made it up the steep dirt bank without killing ourselves or being accosted by police, we then off-roaded it down another steep bank, in order to find our way back on the more orthodox trail up the hillside!

We took a couple more fun detours off the beaten track, laughing at the adventure of it all, and chatting as we climbed.  The Hollywood Actor had just taken part in an obstacle adventure race, dubbed ‘The Spartan Race’, and we talked about it, as well as some of the more adventurous challenges I’ve done prior to 30 Dates by 30.


Finally we rounded a bend and were looking out over the top of the iconic Hollywood sign.  Los Angeles stretched out ahead of us.  The city always amazes me.  It’s just so different to England.  A city in the centre of a desert, even Dodger Stadium is fringed with palm trees.  I love how different it looks to Britain – it’s impossible not to feel on holiday when you’re surrounded by a completely different world.


The climb was hot and sweaty in the midday heat, and really dusty, and my date outfit was ill-chosen for our off-road detours, but the climb made for a really fun date.  We had heaps of opportunities to chat, and the views were definitely worth the thirty-minute climb.  On the way back down we laughed as our perspective on the sign changed – from one angle it actually read ‘OHLLYWODO’, which we decided was the Lord of the Rings version of Hollywood.

Safely back down in the air-conditioned car, we drove a short distance to our next destination.  ‘101 Cafe’, a true American-style diner at the foot of the Hollywood Hills.  I had wanted a quintessential American first date, and I was getting one, seated in diner that looked just like the one from Pulp Fiction, eating Eggs Benedict with a freshly-made hash brown.

The brunch topped any I had eaten in London (but then Eggs Benedict originated in America) and the conversation while we ate was really interesting.  The Hollywood Actor told me all about his different projects, including his recent on-screen demise in a war movie that will hopefully be showing at the Sundance Film Festival.

Hollywood is not just a completely different world because of it’s desert location, and it was really interesting to hear more about the crazy LA lifestyle.

Los Angeles is just as foreign as the movies suggest – a city where everyone is either an actor, a writer or in film production.  (As well as probably being a waiter, a bartender, or something equally mainstream at the same time!)  On Friday night at the baseball we’d sat behind actors talking loudly and at length about their auditions that day, and as I flicked through Tinder options in the LA area a few days ago, almost every one described himself as an actor.

I had laughed with The Producer about The Hollywood Actor asking me to put his headshot in the blog, and The Producer had made clear his friend wasn’t that kind of Actor.  However as we sat chatting about his various acting projects, I asked if I could add his showreel to the blog – as I cannot count the number of times readers have asked me what my date looked like.  So seeing as this is the final date of my 30 Dates Challenge … here’s a little treat for those of you who like to have an image of my date in mind!

I wore – Black cropped trousers, a black vest top, a black lace top and TOMS.  All of which got covered in dust and were way too hot!

He wore – a t-shirt and shorts, and trainers (sensible option!)

We met – at my friends’ apartment, in Westwood, Los Angeles

We drank – water on the hike, orange juice and ‘soda’ over brunch

We talked about – LA, acting, university, travelling, China, Patagonia, adventure races, Everest Base Camp, Kilimanjaro, skiing, London, movies

The date lasted – four hours

The date ended – at 2pm (with me having 10 hours left of my twenties Stateside, and just 2 hours left of my twenties back home in England).

Marks out of ten – 9/10 The hike was a great location for a date.  There wasn’t a cloud in the sky and, as I’ve said before, it’s often easier to chat when you’re not sat face on with your date.  We spent a lot of the date laughing, especially when we got lost just trying to begin the hike.  And then brunch at the 101 Cafe was the best I’ve had out of all of my daytime dates on the Challenge.  LA stepped up to the plate, and delivered!

Next Date?  Who knows!  And who knows what will happen next with this Challenge … but for now, I guess watch this space!  And thank you all so much for reading and commenting over the past three months.  I have genuinely had one of the best summers of my life, and it’s not just thanks to the wonderful thirty men who have volunteered themselves up as First Dates, in London, Reading, Bristol, Madrid, New York and Los Angeles.

You guys ALL rock!

Miss Twenty-Nine xxx

12 Trackbacks / Pingbacks

  1. The Full List | 30 Dates by 30
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