The Henley Boy

I wish I could say that my motivation for this challenge was purely journalistic.  That I had thought of a light, fun challenge to see out my twenties in style, and that was all.

Don’t get me wrong, the challenge has definitely put a grin on my face so far, however there is a slightly sadder reason why I’m throwing all romantic caution to the wind, and  agreeing to fill my diary with first dates for the next three months.

You see, this time last month, I was on The Perfect Date.

After months tentatively internet dating, and spending my time online deleting message after creepy, odd, message, I had started chatting to a guy with actual potential.  Up until this point, I had only ever met up with one guy, who I had met online, and the ‘date’ had turned out to be rather disappointing.  It made me realise how easy it is to form an inaccurate picture of someone, when all you have to go on are text messages or emails.  Words mean different things for different people.  And so I discovered, when my first ever ‘internet date’, turned out to be anything but ‘confident’, ‘outgoing’ and ‘6 foot 2’!

With this in mind, I tried not to get too excited, as Henley Boy began messaging me.  He was someone I had already noticed on the dating website.  His pictures were attractive, and his profile casual, but down-to-earth.  A casual message asking me about a sport I was playing in one of my profile photos led to a 5-hour conversation over the dating site.  A day later, and we were texting.

We texted all of that week, and booked in a date at a fashionable bar in the beautiful neighbouring town of Marlow.

I can still remember the first time I spotted him, as he wove between the cars on the High Street, trying to spot me through the crowd.  He was six foot three .  The perfect height when you’re 5’11” in heels!  He had rower’s shoulders, loose caramel curls, and was casually dressed in a burgundy sweater and dark coloured jeans.

His first words were ‘You look lovely’, and his smile was broad and genuine.

It was like someone had taken a cookie cutter, and formed my ideal man.  Without me even realising what the ingredients should be.

That evening we chatted for hours.  Before I knew it, the bar was shutting and we were being asked to pay our tab.

Normally on a date, I do a fair bit of talking.  In fact, I’ve been on dates in the past where my date has had nothing to say.  But that night, we talked in equal measure.  He told me about his family, his degree, his life in London after university, his Masters, and his friends. We talked about everything and anything, with conversation flowing so easily that sometimes I lost track of what we had begun speaking about.

At the end of the date, he walked me back to my car, and apologised for not trying to kiss me, because he had been ill all week.

Within twenty minutes of leaving his side, he had texted me.  Telling me how much fun he had had.  How I’d been more attractive in person than he had expected.  And how he was looking forward to seeing me again.

The next day at work, I was like a Cheshire Cat!  I couldn’t stop smiling.  The cynic in me had been proved wrong.  ‘Normal’ (hot!) guys did internet date.  And a normal ‘hot’ guy could be as excited about meeting me, as I was excited to meet him.

Henley Boy and I scheduled in a second date, and then spent the next week getting to know one another further.  He began phoning me before bed, and we would chat for hours, about everything and nothing.  It was like being sixteen again!

Every day, I would wake with a broader and broader grin, excited to see what the day would bring.

Two weeks from when we first began chatting, Henley Boy scheduled a last-minute second date.  We had already planned a picnic in Henley for the following Saturday afternoon, but during a call on Wednesday night, HB asked if we could meet for dinner the next night.  He asked if he could come and meet me at my flat, and after two weeks getting to know one another, I felt safe enough to agree for him to join me in my home.

Date Number 2 was completely different to Date Number 1, but equally good.  The first date nerves had evaporated a little, and after a week of daily calls and texts, it felt comfortable.  Exciting comfortable.

We ate, we chatted, we watched a movie, we kissed.  All was good … really good.

Maybe I jumped the gun, but I asked if he’d like to stay over, and that night we kissed and cuddled and spooned.  I didn’t break any ‘third date’ rules (this was Date Number 2) … but things were good.  Really good!

And when I fell asleep in his arms, the romantic in me realised how comfortably we seemed to fit together.

The next morning, Henley Boy cuddled me for half an hour as he ignored his alarm clock.  Finally, once he was out of bed, he returned to kiss and cuddle me through the duvet, and by the time I got up for work myself (two hours later), I had two texts from him on my phone.

I didn’t realise my smile could get much broader, but I was practically bouncing at work that day.  Maybe this was actually it!  Maybe I, the internet dating cynic, was ironically fated to find ‘My One’ online!

A guy who made me realise exactly what I needed in someone else, and what I didn’t.  He wasn’t ‘perfect’, and yet the imperfections were things I realised I had no qualms about.  He was doing his Masters, and not earning much.  He was living back at his mother’s, in a room with floral wall paper, and 80s bedding!  He was younger than me.  But none of that really mattered, because he made me smile from ear to ear!  And he seemed to be just as excited by me as I was of him.

He was my perfect date!

And then, after work that same night, he cancelled Date Number Three.

He said he had too much work on with his Masters, and was suddenly panicking.  I was a bit gutted – I’d been looking forward to the picnic, and the weather forecast for the weekend was looking good, but I tried to be upbeat about it, and offered to meet later on if he got enough work done.

He texted the next day to say he was shattered and going to bed, but sorry about the cancelled date.

And I never heard from him again!

So there you have it … the sad and sorry tale of Henley Boy.  My perfect date. My perfect, heart-breaking date.

I know it was 2 dates.  I know it was 3 weeks.  But in those three weeks … I dropped my guard.  A guard which had been up for a very long time.  I dropped my guard, only to get crushed when I least expected.

And so, frankly the last thing I want to do right now is go on a date!  Because I’ve had my perfect date.  I had three weeks of reading and re-reading every message.  Memorising every snippet of information about a guy, and worrying that I was creating the best impression of myself.  I let myself get excited.  I let myself imagine things in the future.  Future dates.  Him meeting my friends, and my family.

And then, before it even started it fell flat.

But … as my best friends were quick to remind me, these are my last few months of my twenties.  I should be making the most of them.  Not spending them worrying about what I’ve done wrong.

In the weeks that followed my second ‘perfect date’, I ran through every scenario.  Every thing I could have done wrong.  Every possible explanation …

I’ll never know why my perfect date was so imperfect.

But what I do know, is that Perfect Date is not going to be my last!  If you fall off a horse, the best thing that you can do is get back on, as quickly as possible.

And so this week, I get back on the dating horse! (for want of a far more appropriate euphemism!!)  And I will do so in style.  In the next three months, I plan to go on 30 Blind Dates.  I know they won’t be perfect.  I won’t have worried about them for days, or read and re-read every text message.

Thirty Blind Dates.  Recommended by friends, or arranged over internet dating by dropping a few of my strict requirements, and throwing caution to the wind.

Thirty Blind Dates.  Thirty Men.  Thirty stories!

The only requirements …. that I’ve never met them before, they are single, and they are between the ages of 25-35.

After my ‘Perfect Date’, what could possibly go wrong?!

Miss Twenty-Nine xxx

18 Comments on The Henley Boy

  1. Henley Boy Conspiracy theories ….
    1) He is a secret alcoholic (he never drank on our dates, referred to nights out drinking only water), and talked about helping get a friend on AA
    2) He is dead (this is not the case – after a week of silence, I actually googled the Henley obits! and then Facebook message delivery told me he’d read a message I sent!)
    3) He was a thief (I checked the flat a few days after he left, as this was genuinely something that sprang to mind as a possibility as to why he would come over, have such a ‘magical’ date, and never speak to me again!!!!)

    Feel free to suggest more … 😉 Miss Twenty-Nine xxx

    • It is quite possible that his reason was genuine and knowing that if he were to continue seeing you he would continue to neglect his masters degree. Having surely worked so hard for such a long time it would be well worth finishing, could just be bad timing. I’m sure he didn’t expect to meet ‘his one’ as you elegantly put it so didn’t expect to find himself completely besotted by someone as judging by the amount of contact you both had, would seem he was.

      Having been in your position a few times in the past and also nearing 30 myself, it’s interesting to see things from a female perspective. Take your friends advice, all will work out when you least expect it.


    • He’s engaged in a project to date a large number of people in a short space of time, and the rules of the project forbid further dates until project completion.

    • Love that instead of giving up or letting it take you down, you got up and made it a trigger for an amazing experience. I look forward to reading all of the other first dates!

      • Thanks Olivia! It was a lot of fun and inadvertently ended up changing my life! Now Time Out’s global Head of Dating!!! Talk about a mad 18 months! Keep in touch as you read and let me know which date is your favourite! Xx

  2. Perhaps he was using you for content of his blog

  3. so- he turned up to your first date not expecting you to be attractive, then told you to your face that wow actually, WAS worth coming tonight because you are actually better looking than he thought?!… yeah… what a nice guy.

  4. Married

  5. Invited to stay over yet only spooned & cuddled? Unless “cuddled” is a euphemism, it’s a pretty open and shut case in my mind… Or perhaps shut and shut is a better way of putting it.

  6. Hi – I’ve really enjoyed reading your blog, there is so much on there that is refreshingly honest. From a bloke’s point of view it’s interesting seeing into the mind of the opposite sex, I would say that what has bugged me with your Henley Boy experience is this lack of closure. At the very least I do view it as rather rude that he just fell off the radar, I’m now in my mid 30’s, settled down with a partner and kids however struggled to find people when I was younger.

    I experienced a few occasions when people just didn’t respond to messages or calls and I think that if they just aren’t that into you the polite thing to do is to just at least say that. Having said that from my bloke’s point of view I have my theory on what happened. Whilst I do think you are reasonable in tune with what’s going on, perhaps he didn’t feel the way you did about the dates?

    Maybe he liked you but just not that much, when you invited him to stay over, I imagine you had a chat with him about what was, or wasn’t going to go on that night. Perhaps in his eyes he thought then that he wasn’t that into you, however thinking with an appendage that wasn’t his brain, maybe he thought he might possibly get some action. He didn’t and then subsequently thought that if you weren’t going to be that obliging, perhaps he didn’t want to see you again – maybe he was just being a bit of a scoundrel and seeing what he could get whilst not actually wanting to date you……

    • Thanks Matt- the closure thing has definitely made me very careful about how I communicate with other people since then- I try to be as honest as possible and also final, even if I’ve never met them and am deciding its not going anywhere.

      Your HB theory may well be right- the weird part was that he was making all the effort in the run up to date 2, and the date wasn’t completely innocent- if he’d wanted to get laid he most probably would have the next time we saw eachother? Also he’s not been back online dating since our first date, which makes me think another girl is somehow involved? Who knows?! All I know is I’m having a really cool summer as a result!!! 🙂 Thanks again for your comment, really glad you’re enjoying the blog! xxx

      • I think that someone else was involved is a strong possibility, I think it was a site you had a link to where I read a comment along the lines of “then he told me he wasn’t 100% single”, made me chuckle – perhaps that was the situation with HB.

        On another note, it was interesting to read your stuff about POF and speed dating, with the latter I had gone to a few events (a good few years ago) and can’t recall getting anything positive back from anyone there.

        I also met my partner through a dating website, I did find your comment about how many messages you receive interesting, I think that the chances are any female who seems like a good catch is likely to get quite a few messages.

        I don’t think there would be the time to reply to all of them, however from my point of view although I wasn’t just playing the numbers game, most of the time I would send messages and get no reply. Although if they have loads to wade through I can understand why, it was overall a rather disheartening experience to probably only get a response say 1 time in 20 if it’s roughly what someone like yourself responds to.

        Based on that from a bloke’s point of view I wouldn’t recommend doing it, even though I found my partner there – she was one of only a few people who actually sent me a message off her own back. To any female friends I wouldn’t recommend doing it either, based on the amount of messages they’re likely to get, I think it could be hard work separating the wheat from the chaff.

  7. I’ve just found your blog and I love it. I’m starting at the beginning. I am also 29, live in London and am single and turning 30 in a few weeks. This exact same scenario happened to me and I really admire you for not letting it bring you down because it knocked me out of the dating scene completely. I am still scared and worried about getting hurt that I’ve convinced myself it’s easier to not try. However you are right, it doesn’t do me any good to sit around and not put myself out there. So I will start trying again. I’m going to catch up on everything and see what has happened to you on your dates. Thank you for sharing your journey x

  8. Heels Not Needed // October 1, 2013 at 4:29 pm // Reply

    I love this idea! I just went through the same thing! Perfect chemistry and unbelievable sparks and then the slow fade away with dates cancelled. But I am continuing on! Perhaps not quite with the same enthusiasm as you are but close! Haha. Great read!

42 Trackbacks / Pingbacks

  1. ‘Boring Fish’ and the First Day of the Blog | 30 Dates by 30
  2. Introducing Miss Twenty-Nine …. | 30 Dates by 30
  3. Date Number One – The ‘Normal’ Fish! | 30 Dates by 30
  4. The Ideal Man | 30 Dates by 30
  5. The Challenge So Far …. | 30 Dates by 30
  6. The (Good?) Nutter | 30 Dates by 30
  7. Date Two – The One with the Sign | 30 Dates by 30
  8. Date Three – The Burlesque Dancer | 30 Dates by 30
  9. Date Four – The Model Brother | 30 Dates by 30
  10. The Prick, and Plenty of Fishing | 30 Dates by 30
  11. ‘Blind’ Dating in the Modern World | 30 Dates by 30
  12. Date Five – The One with the GSOH | 30 Dates by 30
  13. Goldilocks & The Fairytale Couple | 30 Dates by 30
  14. The Faceless Critics | 30 Dates by 30
  15. Date Six – The School Crush | 30 Dates by 30
  16. Date Seven – The Challenger | 30 Dates by 30
  17. Date Eight – The Fake Pimpernel | 30 Dates by 30
  18. Date Ten – Mr Twenty40 | 30 Dates by 30
  19. Closure and The Eclipse Effect | 30 Dates by 30
  20. Living Life One Day at a Time | 30 Dates by 30
  21. Living Life One Day at a Time | 30 Dates by 30
  22. Speed Date and Dash (Clapham) | 30 Dates by 30
  23. The Bad Date Experiment | 30 Dates by 30
  24. Dating Out of Your Depth | 30 Dates by 30
  25. Date Sixteen – The Argentine Matador | 30 Dates by 30
  26. Date Seventeen – The Pupil | 30 Dates by 30
  27. The Second Date, The Enigma & The Eclipse | 30 Dates by 30
  28. Date Eighteen – The Fresh Prince | 30 Dates by 30
  29. The Return of the Henley Boy – Part One! | 30 Dates by 30
  30. The Return of the Henley Boy – Part Two! | 30 Dates by 30
  31. I’m Single, Get Me Out of Here! | 30 Dates by 30
  32. East End Boys and West End Girls | 30 Dates by 30
  33. Date Twenty-Three – The Oxford Blue | 30 Dates by 30
  34. Date Twenty-Four – The Exhibitionist | 30 Dates by 30
  35. Date Twenty-Five – The Big Kid | 30 Dates by 30
  36. Bridget Jones Meets The Apprentice | 30 Dates by 30
  37. The Henley Boy Effect | 30 Dates by 30
  38. First Date The Musical (a.k.a. My Bonus New York Date!) | 30 Dates by 30
  39. The 30 Dates Challenge in Photos – Part One | 30 Dates by 30
  40. Dating Inspiration | 30 Dates by 30
  41. Playing Boyfriend Top Trumps | 30 Dates by 30
  42. The Full List | 30 Dates by 30

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