30 Dates, One Year On … The Challenger

It’s a year since I did the original 30 Dates Challenge – three months of dating which launched a career change I could never have imagined, and still haven’t quite got my head around!

To celebrate the year anniversary of the Challenge, and also highlight just how much can change in a year, I’ve been revisiting some of the 30 Dates guys, to see what they’ve been up to in the last year.

So far, you’ll have noticed most of the guys are now in relationships.  One is engaged (more on that to come soon!), and a number live abroad.  We also found out recently that one of the boys lost him Mum this year – sadly highlighting just how much can change in a few months, both for better and for worse.

Now, I say I only contacted ‘some’ of the 30 Dates, because to be honest I’m no longer in contact with all of them.  The reality of dating, is that in the normal world, if you only go on one date with a guy, you’re unlikely to keep in touch.  Obviously things are a little different when you’re doing a dating challenge, particularly if the majority of your dates are blind dates with friends of friends.


As a result, I’ve been lucky enough to stay in contact with a number of the original 30.  There are a few notable exceptions.  Date Number One – The Normal Fish – never knew I was doing a challenge … oops! Also, I *may* have told Date Number 20 – The Surprise Package – that I was a restaurant and bar reviewer, to get him to agree to a last minute date at the Ice Bar & Mr Foggs over Tinder!  And for obvious reasons, I attempted to wipe all memory of my dates with The Burlesque Dancer, Stitch, The Pupil and Mr Twenty40 from both my mind and my phonebook!  However, the majority of the other boys are all at least Facebook friends, and I’ve met up with a fair few of them since the Challenge ended.

With all that in mind, I’ve been really lucky that the boys have been so candid answering my questions.  To give you some background, my ‘interviews’ with each of the lads normally starts with me pestering them over Facebook to take part, then sending them a questionnaire with some simple questions about their last year.  Once they’ve returned the questionnaire, I’ll either text or call them with additional questions to get some more info on any particularly interesting areas of their year.  Or in some cases, I’ve met up with the guys and caught up in person.

I’m so grateful to all the boys who have taken part so far.  The reason these articles aren’t in the order which the guys originally took part in the challenge in, is simply due to who replies back to me, and when.

If you’ve missed any of the round-ups so far, here are all the links –

The Attic Mouse

The One With The Sign

The Best Man 

The Hollywood Actor

The Jet-Setter

The Big Kid

Now, if you click on those links, and have a read, you’ll realise just how candid and open all the guys were.  They’re answering questions about their lives, and their love lives, and putting faces to the nicknames I used for them last year, and I have a great deal of respect for that.  I also know a lot of you are loving the feature – so thank you boys!

Anyone who hasn’t wanted to take part, simply hasn’t messaged me back!  (Or in the Voice’s case (remember, he was the ‘token Christian’ I was sent on a date with by the Threads blog) sent a rather abrupt text message saying ‘No’! How very Christian of him! Whoops!)

And so it was interesting to get a questionnaire back from The Challenger, but for him to not have answered most of the questions, and to have asked to continue to remain anonymous.

It’s an interesting one, because who am I to judge?

Just because I put my love life and my face on the internet, and embrace the fun element of the Challenge, doesn’t mean everyone has to – and I guess it just shows how lucky I am that so many of the other boys were willing to put their hands up and admit to being part of what was a really fun and different adventure.  Perhaps one of the reasons the majority of the guys we’ve featured so far have been so happy to talk about their lives, is because they’re no longer single.  As happily coupled-up guys, the 30 Dates Challenge has become a fun story of something they did last year when they were single.  Interestingly the only two single guys in the list above are TOWTS and The Big Kid, both of whom I would describe as comfortable in their single status as I am.

What’s particularly interesting about The Challenger’s response, is that he was actually the first of the 30 Dates who I fancied.  So his reaction to the questionnaire is all the more interesting, as I guess I would assume any guy I’m compatible with, wouldn’t have a problem filling out the answers to the simple questions I sent over.  I guess we weren’t as compatible as I first thought!

Date 6

So who was The Challenger?

The Challenger was a hot guy, who one of my roller derby team mates worked with.  She knew The Burlesque Dancer, and felt so bad when I was set up  on a blind date with him, that she figured I deserved a date with a hottie.  The Challenger piqued my interest before we’d even met.  He was just so confident.  He got his name because he promised in the run up to our date to be ‘the best date ever’ and also said he would be ‘lucky number seven’.

If you’ve never read about my first date with The Challenger, it’s a funny one and worth a read.  We met at The Malmaison in Reading, and a drunk old man, with the same name as my date accosted me in the hotel lobby.  I almost ran away, thinking he was my blind date!

I was super late for my date, because of another man.  This little guy …


Oliver is the son of two of my closest friends, and he was born the day before my date with The Challenger.  On my way out to my date (yes, I was wearing the infamous polka-dot dress!) I stopped by their house to meet him, as they’d just got back from the hospital, and to take their first official family photo!  Needless to say, I was very late to my date, and  Oliver ended up with the nickname ‘Date Number 6.5’!

My date with the Challenge was a good one – we got on well, he was easy to chat to, and he was the first guy I’d remotely fancied since Henley Boy.  But I’d made a massive error in deciding to drive to the date.  He was drinking, and he got really rather drunk, while I had to stay stone-cold sober.  NOT a great mix for a first date.

I think if we’d both been drinking, I’d probably have ended up kissing him, and probably have gone on a second date with him …

And yet when I randomly bumped into him in January (in Henley of all places!), while I was seeing Mr SC, I realised immediately that we weren’t at all right for each other, something his answers to the 30 Dates, One Year On questionnaire probably confirm too!


Before we get to his (very brief) answers, I think there’s an important lesson.  I fancied The Challenger in part just because of his texts.  The man they portrayed was confident and playful.  Whereas the man I later came to vaguely know doesn’t match the man I imagined.  It just goes to show how much you can read into messages.  I’m always telling daters to meet up quickly, because you can’t ever form an accurate impression of someone simply over texts and emails.  And even talking on the phone, you’ll never know for sure if you will fancy them in real life too.

So what has the Challenger been up to in the past year?  At 34, he’s still single, though he hasn’t been single all year.  Whilst this year hasn’t seen him face any dramatic life changes, next month he’ll be moving to Washington DC for work.

It’s interesting as I remember him mentioning on our date that he’d just come back from working in America, and that he’d tried speed dating over there (and done very well thanks to his accent).  I wonder if he’ll end up meeting his future wife out there …?

He didn’t answer any of the other questions about favourite dates, bad dates or adventurers dates, but did say he was glad he took part in the 30 Dates Challenge, and in his words ‘gave it a go.’  He simply explained that he wanted to remain anonymous, and wanted to be careful what information he shared, but apologised that it didn’t make for a great read.

So thank you Challenger for your role in 30 Dates.  You were a breath of fresh air back on Date 7 of 30, and if nothing else, you taught me that I’m a far easier date when I’ve had a couple of drinks! 😉

Again, huge thanks to all the 30 Dates boys, and bring on some more 30 Dates, One Year On!

Miss Twenty-Nine xxx

2 Comments on 30 Dates, One Year On … The Challenger

  1. If he’s moving to DC for work it makes me think he’s gonna be doing something political, hence wanting to remain anonymous! Now I’m even more curious 😉

8 Trackbacks / Pingbacks

  1. 30 Dates, One Year On … The Stallion | The 30 Dates Blog
  2. 30 Dates, One Year On … The Original Pimpernel | The 30 Dates Blog
  3. 30 Dates, One Year On … The Queen’s Guard | The 30 Dates Blog
  4. 30 Dates, One Year On … The Skype Date | The 30 Dates Blog
  5. 30 Dates, One Year On … The Fake Pimpernel | The 30 Dates Blog
  6. 30 Dates, One Year On … The Fake Pimpernel | The 30 Dates Blog
  7. 30 Dates, One Year On … The Enigma | The 30 Dates Blog
  8. 30 Dates, One Year On … The Ones Who Got Away! | The 30 Dates Blog

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: