A well-dressed Where’s Wally

After my second date with the Whippersnapper, I was in a dreamy daze, having just had the best kiss of my entire life. However, within about 10 minutes of returning home, I started a conversation with my ex-boyfriend about who the clump of drain hair on the edge of the bath belonged to.

Even after only two dates, I knew I really liked Whippersnapper. I had such a great time with him, and I felt like he was really similar to me, in lots of tiny ways. My worries about the age-gap had disappeared, and it barely seemed relevant, (apart from when I said something in passing about a CD Walkman and eventually he said “oh! the thing with the CD and then the headphones?”).

However, I’m ashamed to say that the next week, I had a one-off reunion gig with the Young Jaguar. For some reason, I arranged to meet him for a friendly drink, and I’d managed to convince myself that Whippersnapper was on a date himself. This was because he had said in passing that he was busy on Tuesday, but hadn’t mentioned what he was doing, and I hadn’t asked. My antics with Young Jaguar seemed like the only reasonable course of action, when confronted with evidence as iron-clad as that.

On my way to meet Jaguar, I mentally prepared a speech reiterating how little we had in common. However, when I got there, he annoyed me much less than I expected and there were cocktails. At one point, we were looking at the menu together and he held my hand and it felt surprisingly nice.

He kissed me on the way to his flat. It was precisely at that moment I realised I didn’t want to have sex, but I’d already suggested I would, and I felt too polite to abort it by then. We got to his flat and he managed to unzip my dress while I still had my coat on, which irrationally annoyed me. All I could think about during the sex was how much I like Whippersnapper. I felt horribly guilty for having sex with someone else.

Afterwards, I thought ‘How long do I have to stay before I can go home?’ and felt horribly guilty towards poor Young Jaguar. He’s a nice chap, and he deserves sex with someone who really likes him, not this. We sat and watched TV. I think I might have Coeliac’s Disease or IBS and that night, my stomach had turned into a tiny digestive fracking site. We were sitting on his sofa with his arm lying across my stomach. He must’ve felt the vibrations and explosions ricocheting around. I kept trying to nonchalantly move into a position that promoted all of his limbs being away from my stomach, but his hand always seemed to find its way back to my tummy. It was like one of those little robot vacuums that always goes back to its charger.


After I decided the requisite amount of time had passed, I said I needed to go.

There’s a mirror by the front door of his building. I checked my reflection to make sure my hair didn’t look like the hair of someone who had just had sex, as my ex-boyfriend still didn’t know I was dating. I added my ex-boyfriend to the mental list of people I felt guilty towards.

The next evening, Whippersnapper (WS) and I were texting each other. I had just got on the train home from central London, after having dinner with a friend I hadn’t seen for ages. This friend was male. As soon as I revealed I’d just had dinner with a boy, I decided to add more details, to demonstrate that this boy was definitely not a love rival.

“My friend used to be a bit of a rogue, but I’m so pleased because he might propose to his girlfriend”.

WS replied saying “I used to be a bit roguey.”

“Really!” I replied. My Potential Heartbreak klaxon started going off. What does this mean?

“Were you a rogue?” He asked.

I thought about the fact I had sex with someone else within the last 24 hours, and said “who said I’m not a rogue now?”.

The morning of our date, I felt so excited, I couldn’t stop smiling. I was going to meet him straight from work this time, so I had to choose a dress that was believable as a work outfit, and wear it to work, but that also absolutely reminded him about sex.

Although I had started the day feeling excited, by 4pm, I felt like I was about to go into an exam. There were some work drinks, which I had inexplicably agreed to go to first – some nonsense about giving him the impression I’m in demand and won’t necessarily change my plans for him. I spent about 15 minutes in the pub with my colleagues, listened to about 1% of the things people said, and then shot out to the tube.

I got to Embankment and he had already texted me saying he was there, but I couldn’t see hide nor hair of him. I phoned him and he described where he was. I went outside, and found him incomprehensibly nestled in behind a flower stall. I never would have found him if I hadn’t known to look there!

I remembered not being able to find him at Westminster, and then missing him outside the Pizza restaurant.

This guy is terrible at waiting for me in logical places! He’s like a well-dressed Where’s Wally. 

He was wearing a really cool coat I hadn’t seen before.

“You look great!” He said. We kissed, and I went in for a full snog (especially after the success of the Garden Kiss), but he went in for a low-key kiss on the lips, so I felt like a bit of a dick.

We walked along the South Bank for a bit, and then went into a pub. I found a table and he waited to buy our first drinks, and I realised I was already having such a great time. He came and joined me. There were some television screens in this pub, and Donald Trump was on TV. We talked about politics for a bit, and he had all the correct opinions about everything. He told me that he had really looked forward to each of our dates so far, and had been really relieved each time I said I wanted to see him again.

I hadn’t seen him smoke before, but tonight he did. Apparently, lots of girls on his previous dates disapproved of smoking. I’ve never smoked – I would love to, because it makes you look cool, but I’ve never been able to get past the coughing fit. I think in a perfect world, no one would smoke, because it kills you, but I don’t think it’s my place to disapprove. I’m very grateful to the disapproving previous girls though, because all I did was cheerily say “do what you like!” when he broached the possibility of going out for a cigarette, and it seemed to blow his mind.

We started out talking about general things, but after a while, he asked me about my previous relationships. He had already given me the gist of his romantic CV on the last date (one long-term girlfriend), although I wanted to find out more about this Rogue Business.

He already knew I was living with my most recent ex, but I had been thinking I wanted to tell him that I had an ex-boyfriend who died. I’ve learnt from experience that bringing up dead exes can be a bit of a boner-killer. However, it’s an important part of my backstory. Over the last week or so, whenever I was in the shower, I kept finding myself working out how to describe it in my head.

So I told him. His reaction was just right – it wasn’t too big or too small.

I asked him about being a rogue. It turned out that he used to be very insecure about his appearance, for various reasons (which is surprising, as he is definitely at the top end of the attractiveness spectrum). When girls started taking an interest, he began having a lot of one night stands. He said he did it to reassure him that he looked OK. It sounded like he wasn’t dishonest or misleading to anyone. The way he talked about it made me like him even more. He was so open and self-aware.

He said “I hope you don’t think this is an extension of that. I’m looking for something more meaningful now.” He added “I’m not looking for a super-serious relationship, but I’d be open to it, if it came along”.

It was by our third drink that I realised he was quite a bit more drunk than me. Not embarrassingly so, but I enjoyed being the more sober one. It wasn’t that surprising, as he was drinking large glasses of wine and I was drinking gin and tonics, so he was having 3 units for every one of mine. He was dishing out a lot of compliments, which I was very much OK with.

We talked about our worst fears. Now I had told him about my ex-boyfriend’s death, I felt like I could tell him the lighthearted answer (spiders) and the heavy-going version (fire). He told me that he’s afraid of flies.

After my massive oversharing on the second date, I was trying really hard to keep my ridiculousness to a minimum, such as catching these words before they slipped out:

  • when talking about how difficult contact lenses are to put in, I didn’t say “it can’t be more difficult than a mooncup”
  • when he said “another thing I really like about you is your skin. You’re like an English Rose” I didn’t say “oh, this is just a lot of Roaccutane and expensive makeup”

Later on, the pub was getting empty, and I went outside with him for his cigarette.

“So, how did it end, the being a rogue?” I suddenly thought to ask. We were sitting in the pub garden at a table, both on the same side, facing the same way.

“I ended up getting herpes.” He replied. He looked at me to check what my reaction was.

“Herpes! Wow.”. We talked about this for a bit. I already knew that one of the worst things about herpes was that once you have it, you always have the virus and could give it to someone else, even when your symptoms have gone. I can’t remember what I said, but it must’ve been reassuring, because he said “I was really worried about telling you. I thought you might think I was dirty or something.”

“Of course I don’t think that!” I replied.

He said “I think you’re the coolest person I’ve ever met.”

I was about to accept that compliment, but then I thought about how cool I actually am, and said “that’s not really true, is it?”.

“I meant you’re the most non-judgemental and cool.”

This was enough herpes chitchat, I wanted him to kiss me now. I gave him a meaningful and encouraging smile. He smiled back.


I put my hand on his thigh.

He lent across and kissed me.

6 thoughts on “A well-dressed Where’s Wally

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