Date Fifteen – The Booby Prize

It’s not every day that you have to board a plane to go on a date with a guy!  No, I haven’t been whisked away by a multi-millionnaire with a private jet!  But my 30 Dates before 30 has gone international (and this time next month will also go intercontinental!)

Signor28, a friend from university, had been following the challenge from its infancy.  When he emailed me to let me know how much he and his office colleagues had been enjoying the blog, I asked if he had any single friends in London who might be keen to take part.  Signor28 had been living in Madrid for the last four years, and admitted that the only single Londoners he knew were mutual friends.

A passing comment about finding me dates in Madrid led to me booking flights out to visit him for the weekend, as we hadn’t seen each other for the best part of six years, and it seemed the perfect excuse to catch up.

It’s interesting, because when I was at university, Signor28 was probably one of the most eligible bachelors I knew.  Tall, confident, sporty and attractive, he never had any problems with the ladies!  In fact, it was something of a surprise to arrive in Madrid and find him so happily smitten with his relatively new girlfriend.  I guess it’s a sign that even the most established bachelor can change his spots upon meeting the right girl!

Signor28 plays for a local Madrid rugby team, and had spent the week running up to my arrival testing the water for dates.  He told a variety of stories to explain why he was fixing me up with random men on my trip to Madrid, and at the start of the weekend was unsure whether I’d be going on four blind dates, or none at all!

My night in Madrid would have made for a cool blind date all of its own.  Signor28 showed me a beautiful pop-up rooftop bar, open only for the summer, on top of a local museum.  We sat on a fake grass landscape, drinking our drinks from a table which doubled as a light box, and looking out at the panoramic views of the Madrid cityscape at night.  It was then off to a street party in a southern quarter of the town, where I first met The Booby Prize!

As I’ve explained before on the blog, if you’re 5’8″ or taller, and female, blind dates can be a bit of a minefield, because there are a surprising number of guys around who are that height or shorter.  Early on in my challenge I realised wearing high heels on a blind date was an unnecessary risk, as I was just setting myself up to awkwardly look a guy directly in the eyes all date, or worse, look down on him.

As I touched on in my last post, I broke the rules slightly by inadvertently bumping into the Booby Prize the night before our date.  It was at this point that I realised Signor28 had probably been living in Spain too long, and forgotten how to measure in feet and inches! The Booby Prize was just about scraping 5’6″.  That first night I had been wearing heels, and so I was careful to wear flip-flops on our actual date.  However, I was still quite noticeably looking down on my date every time we talked, which made me rather uncomfortable!

BP was hammered when we first met, and repeatedly mentioned how he would be my Booby Prize the following night (hence the name).  It was only when I met up with him that I realised why he had kept saying that.  Signor28 had told the Booby Prize that I had lost a bet and that was the reason why I was having to go on thirty blind dates.  This not only meant that he frequently referred to himself as a Booby Prize, but also meant he thought I was just making up numbers with any old date, and hadn’t really put much thought into the ‘date’.

We met at the Metro station Iglezia, and I assumed he had a specific destination in mind, however he appeared to be playing it by ear.  He suggested cocktails at a bar which didn’t actually serve cocktails, and had a rather unpicturesque terrace on a quiet pavement corner.  The second bar we then tried was closed for the holidays.

Seeming out of ideas, he suggested an indoor beach.  Keen to add a different spin to the evening, I agreed to a cocktail at the indoor beach – a bar filled with sand and sun lounger-like beds and seats.  We sat at the bar, and given the setting, I opted for a pina colada, while BP ordered an old fashioned, which rather bizarrely came in a martini glass full of crushed ice.


We chatted over cocktails and then headed off in search of a restaurant.  Eventually BP decided upon ‘El Pez Gordo’ – the Fat Fish, in the Barrio Malasana area of Madrid.  It was a small restaurant, decorated with photos of jazz singers.  The food was basic – a dish called Migas, which is made of breadcrumbs and pig fat, cod croquettes, and tempura aubergines and courgettes covered in a thick treacle-like honey.

The food was all very rich and fried, and not really to my tastes, though the atmosphere was nice enough.  We chatted into the night, and The Booby Prize was interesting and engaging.  At around 2am we walked back to the main street, where The Booby Prize helped me into a taxi.

I’m not going to lie, I was really quite disappointed by my first Spanish date.  Having spent the day enjoying some of the amazing sites and bars and restaurants that Madrid has to offer with Signor28, I was fully aware how cool an evening in Madrid can be, so it was a shame that The Booby Prize had chosen to make no effort with the date.

Anyone planning a date in Madrid, I would highly recommend a visit to Retiro Park – where you can hire a rowing boat for just 7 Euros, and row around the man-made lake.  I would also recommend finding a rooftop bar with a good view of the city.  With Signor28 and his girlfriend, I ate in a number of places with great tapas, including Mercado San Miguel, where we dined on oysters and champagne, and enjoyed Vermouth cocktails, and the chain Lateral, where we enjoyed tapas topped in brie and steak.  I wasn’t particularly impressed by Migas, or by what the I saw of Barrio Malasana, however it’s hard to tell from sampling only a few bars and restaurants.

We met – at the Iglezia Metro station

I wore – a blue summer dress decorated with a bow print, flip-flops

He wore – a pink and white striped dress shirt, shorts, brown leather shoes

We drank – an Old Fashioned, Pina Colada, diet coke, beer, water, caramel liquor apperatifs

We talked about – Spain, how long he’d lived here, work, womanising (!), relationships, the challenge, Henley Boy (!)

The date lasted – 4 hours

The date ended – when he put me in a cab back to Signor28’s house

Marks out of ten – A very average date.  BP was interesting enough to chat to, but by his own admission hadn’t really made a great deal of effort, and I didn’t enjoy drinks or dinner.  Having seen what amazing things Madrid has to offer, it was quite a disappointment.  6/10.

Next date – Tonight (Sunday) with another of Signor28’s friends …

Hopefully this one is worth the plane flight! 😉

Miss Twenty-Nine xxx

1 Comment on Date Fifteen – The Booby Prize

  1. Unfortuanately this is the kind of blind date most of us go on regularly. If they know about your challenge, especially lately, the men seem to make a huge effort which just doesn’t usually happen on first dates in my experience. Therefore, I am glad you are considering doing things a bit differently for the rest of your dates. 🙂

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