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

16 Comments on The Henley Boy

  1. Hello. I ‘ve just been reading a few of your posts but was especially interested in this one. By the sounds of it, we’re the same age, the same height and have exactly the same outlook and goals when it comes to men.
    In fact, the situation you describe here with Henley boy is almost identical to something that happened to me with a guy this summer. Every woman I know has had a guy do this disappearing act on them. I was heartbroken when it happened to me recently but, like you, I’m not the sort of person to let myself dwell for long.
    I always have some crazy plan or project for how to get more great guys to go on a date with me.
    I also have a blog, which is a bit similar to yours:
    I’m going to follow you on Twitter!

  2. I kept thinking about your experience with Henley Boy and I suddenly realised it seemed to confirm a theory that I have been feeling for a while now. 

    From what I can tell from this blog you have a great job, you’re intelligent, you’re accomplished, you’re well-travelled, you’re condfident and you’re attractive. Henley Boy was younger than you, a Masters student (ie. without a proper job), not earning much and living with his mother. 

    Although none of those things mattered to you, they probably subconsciously mattered a great deal to Henley Boy.

    Something very important for men is that when they’re with a woman they’re able to ‘feel like a man’ with her. They need to feel like they can offer the woman something and protect her. If you’re familiar with Matthew Hussey, it’s something that he talks about in a lot of his videos.

    If a guy finds himself in a situation with a woman where he doesn’t know what to do to impress her, I really believe he can start to feel in secure, start to panic and decide to just bail out completely.  I think that’s probably what happened here.

    Inspired by all this, I’ve actually written a blog post about this theory and you get a mention in it too!

    I saw your comment that Henley Boy reappeared a few weeks later. What happened then?

    • Thanks Estelle, have seen the posts and commented on your blog 🙂 if you check out the three posts entitled ‘Return of the Henley Boy’ (parts one through to three) you should see how it all ended… Unfortunately not very well! But I guess I still have a lot to thank him for! 🙂 xx

  3. Woah. This is so weird. I am reading this and it’s like classic book example. He acts perfectly sweet and romantic and then he never calls again. Was there a rule againsst you contacting them first?

    • *shrugs* he contacted me first in the first place – which was one of the reasons I was so excited! I did text him a couple of times, and email him once, he just never got back to me …. Definitely worth reading the various Returns of the Henley Boy across the blog!! 🙂 xx

  4. Exactly the same thing happened to me two weeks ago. Great first and second date (introduced me to some of his friends), stayed over on the second date but nothing happened. Said he wanted to go on a third date, text me and then he never text me again. I just don’t understand what I did wrong! I’m very tempted to demand an explanation/want closure! Great to see that your blog’s going well though 🙂

    • Unfortunately Grace, after six months of investigations and surveys, I think the realities is that boys just get scared off when they get attached. The Elastic Band theory in Men are from Mars is a pretty good illustration 😦 chin up hun, one day we’ll meet keepers who aren’t scared off by the fact we excite them!!!! Xxx

  5. After reading about your trigger date I think I’m going to become quite addicted to reading your work! On to date number 1 – great stuff!

  6. The driving force behind his behaviour is exactly the same as your response to him: ego. You went off on a dating spree, not caring a jot for who you met and their feelings. Guess what? Him too. Take it from a self-aware man who used to do exactly what he did…he was looking for female approval to boost his damaged self-esteem, probably caused by a love he lost too. I would actually go further to say that he had gone out his way to develop his “player” skills…I can see exactly how he played you.

    • Hmm- ‘not caring a jot for … their feelings’ – you know my dates knew about the challenge and volunteered?! I wasn’t leading anyone on. And I wasn’t calling anyone every night, establishing false hopes! Bit of an unfair parallel I think. But each to his own opinion! Thanks for commenting xx

      • Your motivation was the same; to even the score. To validate yourself by showing the world that you could attract lots of men; that he didn’t matter because there were plenty of others to take his place…Whaat?! You deny this?! 🙂

      • Yeah I definitely deny this- I wasn’t trying to attract guys, it was a fun challenge to remember that dating was fun. If I wanted to even the score I would have anonymously gone online, talked about how many guys loved my profile and then actually messed guys around, which I’ve never done. From date 2 I was completely upfront and open about the challenge and saw it as a way of finding fun places and making new friends – something I did- at least 10 of the guys are now friends I regularly chat to or meet up with.

      • It wasn’t about what he did to me with regards to attrctiveness or self-worth, I realised it wasn’t a direct reflection on me. It was about how he made me lose hope in dating, and not want to get out there meeting people again, for fear of being burned. Xx

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