The Second Date, The Enigma & The Eclipse

When I first started this challenge, other than to ask ‘Why?’, the most common question people would ask me was what I would do if I met someone I liked.  Would I continue the challenge? Or would I put it all to a halt for the sake of Mr Right?

To be honest, I didn’t think I’d fancy any of my dates.  I know how picky I am, and I knew how much it was going to take for me to get over the disappointment of the Henley Boy situation. And so I would simply reply that I would wait until the Challenge was over (i.e. until I turned 30) and them go on a second date with him.

Second dates are a funny thing.

Before this Challenge I’ve always known pretty quickly if the guy I’m on a date with is someone I would consider for a second date.  In a normal dating situation I tend to learn a lot about the person before the first date.  It’s why I met up in person with so few of the guys I met online dating- often over a few exchanges on the dating site I would know whether I could see us getting on or not.

With Blind Dates it’s really different- you only have a few short hours to judge a guy on, and determine whether you could see it going anywhere. Obviously physical attraction plays a big part in that. I’m not ashamed to admit that I couldn’t ever see myself dating someone whose clothes I didn’t want to rip off (because that’s all part of the fun, right!).  So  with the guys I’m really not physically attracted to in the first place, it’s genuinely quite easy to know where I see the date going.  With the exception of The Argentine Matador, none of my dates have been completely jaw-drop gorgeous, however a fair few have not been unattractive – the kind of guys who you know will grow more or less attractive depending on whether you like their personality.

Of my seventeen dates so far, I’ve said I would go on a second dates with a handful of them.  Interestingly a lot of dating advice suggests you should never just go on one date with someone.  If this is someone you’ve agreed to go out with face to face (as opposed to blind) I can understand. However arguably with a blind date it’s a little bit different? Sorry but you couldn’t have paid me to go on a second date with either the Burlesque Dancer or Mr Twenty40!

But I can see the merits in a second date with the guys who I wasn’t completely sure about.  The ones who I got on well with on a personal level, and who didn’t physically disgust me! 😉

However, because I didn’t automatically know whether I fancied them or not, I was more than happy to brush second date suggestions away to September, and carry on with my serial dating challenge.

And then there was The Enigma!

Whenever I write a blogpost, I read and re-read the post several times.  The first publication is normally peppered with typos and spelling mistakes, so it normally requires a few revisions. Every time I’ve read back my date with The Enigma it’s put a smile on my face! When I first met him outside Euston Station, he wasn’t someone I would have necessarily picked out of a crowd, though I’m beginning to think my appreciation of guys directly correlates as to whether they’re pretty enough be cast on Hollyoaks or not! He wasn’t unattractive though, and was wearing an outfit that was very ‘me’. As the date progressed  the fact that his ideal date was also my ideal date was definitely a draw, as was the forced intimacy of all the different aspects of the rather unorthodox first date.

I omitted one thing from my blog post about Date 12 …. He was (and still is) the only guy who I kissed at the end of the date.

When you’re dating thirty different guys in a short space of time (and communicating with far more than thirty, as to be honest a lot of dates fall through before I ever meet the guy), you have to have some kind of ‘system’. And so when a guy gets in contact with me, and I save his number to my phone, I save it in the format ‘Name (Referee)’ e.g. Sam (Kate).

After my first date, I began a tradition of changing the date’s name on my phone to match the blog, so my phone book contains a whole list if contacts whose names begin with the prefix ‘The’.  The One with the Sign, The Attic Mouse, The Fake Pimpernel, The Original Pimpernel

But with The Enigma things were a little different … In fact I actually joked with him that he was the only guy I’d dated on the challenge whose name was just saved to my phone as his actual real name!  Which may sound like nothing, but as far as 30 Dates by 30 goes, that was a really big deal!

The night of my first date with The Enigma, he texted me shortly after I got in the cab, and right up until I fell asleep that night.  I arrived at my friend’s house, excitedly babbling about what a great guy I’d met, and when the blog post went up the next day, he sent me a text to say it was the best thing he’d read in ages, and we kept in touch over the next two weeks, texting most days, and arranging a second date,

This is where I broke my own rules.

I realised The Enigma was different to the other guys I had talked about going on second dates with, because I didn’t want to wait until October to see him again. And so I asked if I could repay the favour of such a great date, and be in charge of organising a second date myself, as a complete surprise.

To be honest it was quite nice to have the tables turned, and to ensure I’d be doing something on a date which I wanted to do. Because of the date restrictions, I opted for a sunset walk over the top of the O2 (Up at the O2) followed by dinner at the OXO tower,  (I’m sure I could have come up with some cryptic clue about naughts and crosses, but alas  I’m merely Miss 29 and not the Enigma!) I sent him a few misleading teasing texts every time he tried to squeeze what we were doing out of me, and joked that he needed to be under 21 stone to take part.  There were a few more crazy and imaginative options I could have chosen, but none would have fit together so well time-wise, and these were both things I’d always wanted to do on a date, so I reconciled myself to the fact I was probably not going to ever rival Enigma’s 10/10 date score, but I knew it would make for a fun and enjoyable date.

And that it was – Up at the O2 is possibly the biggest rival at the moment to heading up the Shard (which I did with The Model Brother) and I definitely preferred scaling the O2.  It might be lower, but it’s more of an actual activity rather than simply getting into a lift.  The Enigma and I jokingly raced each other, trying to work out the complicated carabina system (the mechanisms locked every time you reached a metal post on the way up, unless you held the the clip at a special angle, which neither of us completely worked out.)  Knowing that sunset was at 8.15, I had booked the 7.45 tour, but the tour guide was in a real rush to get us up on top of the former Millennium Dome, and so we quickly watched a briefing video, downloaded the phone app (which was rather awful!) and were rushed into harnesses and over shirts which resembled scout uniforms!


After a very quick verbal introduction and some official photos, we were rushed up on top of the O2 and onto the viewing platform, where we spent half an hour watching London descend into night.  As the lights appeared around the city, we took photos in front of the views, and the tourguide introduced me to the panoramic capabilities of my iPhone.  Eventually, we headed down, laughing about the Enigma’s lack of balance, and the fact that neither of us were particularly photogenic, especially in the panoramic photos.


We descended around the back of the dome, having learned that it would take 15 minutes for Niagra Falls to fill the O2, and that the UP app is rubbish – the photo we took using it was almost in complete darkness! (Though it does mean I can put a photo of the Enigma on the blog and he can maintain his anonymity!)

photo-2 copy


After an impromptu walk around the O2 (we got a bit lost trying to find the tube station), we headed off to destination two on my planned date- Southwark Tube station.  The Enigma was still playing the game, and if he realised we were going to the OXO tower, he didn’t let slip until we were literally at the foot of the tower.

The restaurant is gorgeous. We waited briefly in the bar area, and were guided to seats by the floor-to-ceiling glass windows, overlooking the most picturesque section of the Thames at night. The OXO restaurant is one of the best restaurants I’ve been to in London, the menu was phenomenal, the service pristine, and the views breathtaking.


We talked and drank into the night, splitting our starters as we had in Dans Le Noir, and teasing eachother about our interactions over the previous two weeks.  At the end of the date, well into the early hours of the morning, it seemed sensible to spend the night in London rather than take the 1.5hr stopper train home, and so I kind of invited myself to stay over at the Enigma’s  flat, not that he took much persuasion!

Back at his flat, things were pretty innocent (this challenge is complicated enough without trying to sleep with any of the 30 guys!) but we chatted and kissed late into the night, and if I’m honest I found myself wondering if I’d actually met a future boyfriend through this crazy dating challenge. He was interesting, and witty and kind, and a real gentleman.

The only alarm bells really rang when I asked him when he had last slept with someone.  He went quiet, and considering how straight-laced he had seemed, I assumed he might say quite some time ago, or even suggest he was a virgin.  I was nowhere near! He told me that he’d had a one night stand that previous weekend (while we’d been texting, and while I’d been in Madrid).  He’d mentioned before how he’d enjoyed his time as a singleton in London, but I guess that black and white reality of what he had just said rammed home just what he’d meant.  And equally made me realise maybe I wasn’t that special.

Obviously with 14 more dates to go, I could never fault the guy for ‘seeing’ someone else, but whilst I had been on other challenge dates happily chatting away about my best date so far (and even telling my dates that I was going on another date with The Enigma) , he had slept with someone else, knowing we had a second date planned.

For me the obvious next question was to ask him what he was looking for.  The weird part about meeting someone on this challenge, is that all they are signing up to is one first date.  It’s not like meeting someone on the internet who is clearly ‘looking for a relationship’.  When I asked him, he rather honestly replied that he wasn’t sure.  And then apologised for being honest.

I guess as a girl when a guy says that to you, you hear the bit you want to hear.

He hadn’t ruled out the idea of a relationship, and arguably the fact he might be a little more difficult to get probably made him more attractive.

That’s awful isn’t it?  When the nice, polite gentleman seemed to fancy me, I ummed and ahhed slightly about how much I fancied him, and yet when he got a bit of a player edge, and seemed a bit harder to pin down, suddenly I realised I rather liked him!

And the thing is, I think most girls probably think like that too!

I spent the night at Enigma’s talking and kissing, got very little sleep and then began a rather long commute into work the next date from Central London back out into the sticks.  I left on what I considered cute, rather promising terms (he tried to get up to walk me to the Tube station, and I refused to let him walk me there telling him to stay in bed, and so we stood kissing in the doorway of his flat), and then we texted over the next couple of days.

On my date with The Pupil, all I could think about was my dates with Enigma.  As I told The Pupil what worked and what didn’t when you go on a date, I knew most of the time I was talking about Date Number 12, and I couldn’t help smiling when the dessert I ordered was similar to the one I had at the OXO tower. ( I’d eated ‘Tonka Pana Cota’ at the OXO, and the Enigma had dared me to order the funny sounding dish without grinning at the waiter.)

And so on Friday night, I came home, and posted about my date with The Pupil, and obviously let slip that someone I had met on this challenge had managed to have the Eclipse Effect over Henley Boy.

I had been unsure how I would write up the Second Date, or whether I would even put it on the blog.  When I discussed it with friends, some suggested it would spoil the challenge and the blog.  Others thought it would add to the blog – how would I go on 14 more dates when I clearly really liked Date Number 12 enough to want to stop?  I considered asking him to do a write-up of me organising a date, and to even mark me on my date arrangement skills.  I toyed with the idea of telling you all that I’d been on a second date, but not revealing the identity of the man.

And then, yesterday morning, the Enigma solved all my dating blog dilemmas.

On my way into London to meet Date Number 18, I received a text message from The Enigma.

‘The chat we had the other night – the way this has come about is a bit unexpected, & I’m not looking for anything serious.  I’ve had two really fun evenings but I don’t want to mess you around, especially during your challenge.  I’m sorry, I think I should take a rain check on next week? X’

And so I got a 10/10 date, and the eclipse effect.  I let myself start getting excited about a guy again, only to be let down almost as quickly.

I can’t blame him – he was very honest with me, and at least had the dignity to tell me (which is more than I ever got from Henley Boy), but I’m not gonna lie that I’m not gutted.

People have asked me what I hope to achieve from this Challenge, and I was adamant I was never looking for a boyfriend, it was all just meant to be a bit of fun.  If I could choose between getting a book deal or a husband off the back of 30 Dates by 30, I would have always chosen the book deal …

But do you know what?  For a couple of weeks, it was really quite cool entertaining the idea that I might have met my next boyfriend in this crazy random way.  It would definitely have made for a cool ‘how did you meet’ story! ‘Well, I asked his colleague’s girlfriend if she knew any guys I could go on a blind date with, and so he locked me in a room and made me eat in the dark!

But that isn’t what this Challenge is about … and I guess by breaking the rules, I realised the reason this challenge is so fun is because it’s JUST about first dates.  Once you get beyond a first date, you start really messing with feelings and expectations.  With a first blind date, there are none.  And sometimes that’s a lot safer.

And so, I have thirteen more blind dates to go …. let’s just hope I get at least another 10/10 so someone can eclipse The Enigma! (who, by the way, also happens to come from Henley!!!)

Miss Twenty-Nine xxx

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3 Comments on The Second Date, The Enigma & The Eclipse

  1. Sorry to hear this, how disappointing. Can’t have been a pleasant text to receive but thank goodness you didn’t get the vanishing act. Is there anything more demoralising?

  2. We all speak in forked tongues at times Miss29, and not many people would be confident enough to start a relationship with someone knowing that they are going to be dating at least 13 more people imminently! I think it is your timing Miss29, rather than anything else. Do not despair! Your next BF will be around the corner.

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