28 dates on 28 different dating sites. What could go wrong?

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28 Dates Later, by Willard Foxton: Part Ten, the Cougar

In which Willard dates an older woman.

The other type of Cougar. Photograph: Getty Images

Back when I was starting the blog, I asked friends to email me any strange dating sites they might have seen or been on. Obviously, this was all on Facebook, and a huge list of dubious dating sites presented itself fairly rapidly—especially from my more, erm, alternative friends. I can't even remember the name of the most disturbing one, but it definitely was for people who get turned on by smothering each other in baked beans. But this was suggested by a man who lives year-round in a camper van and has a proudly open relationship. I mean, normal people don't do that sort of thing, do they? 

Thus, I was rather surprised by one very stylish older lady who I once worked with suggesting "Have you thought about CougarDate.co.uk? Lots of the divorced women at Jessamy's playgroup swear by it". She claimed it was a haven for divorced London ladies who lunch—the sort of Sex & the City woman in her late thirties who are looking for younger men for a bit of a fling. Now, I'm hardly the 19 year old Brazilian bartender/model I'm sure most of these ladies are looking for (the site divides you into "Cougars" or "toyboys"), and I'm not really looking for a fling but it seemed worth a roll of the dice. For the research, like.

I'd dated older women before—notably the farmgirl recently—and one of the big issues is always children. Once, in my mid-twenties, I'd dated a woman who had a teenage daughter, and it is weird, having a person with real opinions who you befriended as you date their mum. That particular relationship had a very embarrassing moment where the mum in question asked me to do her doggy style while she watched Pride & Prejudice, which would be bad enough anyway, but then having to talk to the depressingly worldy teenager the morning after was, as you can imagine, excruciating: "I heard Mr.Darcy last night. You got lucky then?"

That said, Samantha is definitely my favourite character in SATC, so I took the plunge. I'll confess I was a little bit sceptical—most Cougar sites I've seen look like fronts for identity theft, or pure sleazy hookup sites. I've always been adamant that this is a dating blog, not a sex blog (I'll leave that to Girl on the Net), so I wasn't really looking for a one-time sex thing. That said, my ex-boss assured me it was full of women just like her, and she's totally a woman I'd love to date, if it wasn't for her sexy handsome husband. So, on the basis of "no-one who wears Laboutins & loves independent film could be wrong" , I fired it up, created a profile, and had a look. 

It's quite unusual, in that it's very location based. You can turn on a map of your local area, and it will show how many "Cougars" are around you at that given time. It's the closest I've seen to a heterosexual version of notorious (and amazing) gay hookup app Grindr. So, I turned on the map. If what my wise ex-boss had told me was true, Chelsea should have been a hot zone. I waited for the map to load, confidently expecting to be disappointed. But oh no. Once the mapping app got going, it lit up like the motion tracker in the film Aliens.

As you can see, there are literally *hundreds* of women using this in Belgravia alone. Now, it was just a matter of finding one who'd go on a date with me, rather than just pin me down & milk me inbetween the nanny leaving and her husband getting home. 

It's very clearly a fairly sex-oriented site—lots of the pictures are overtly sexual, with stockings, suspenders, and low cut tops a particularly common trope. After a morning of looking and messaging, I spotted a lady with a very artful set of profile pictures, where she'd cleverly obscured her face with a variety of large vintage cameras. I dropped her a line complimenting the photography, and we started chatting.

We agreed to meet up down on the London waterfront, at a lovely pub called the Blue Anchor on the Hammersmith waterfront. The weather was unseasonably nice for February, so we sat outside, talked and she smoked. She was very attractive, funny, and very thin indeed. She had white wine, I had cider. We talked about her career—she had a fascinating job in the creative industries, that I can't really talk about as it would identify her all too easily. She had seen a bunch of the documentaries I had made, so I treated her to a couple of tales from the good old BBC days, which had her "laughing until her face hurt".

We talked about previous relationships—she'd read the blog, so asked for the full details on my disastrous previous form, and I filled her in on the details. I asked her how someone as successful & lovely as her had managed to dodge the wedding bullet. She was in her early forties, so well within the bracket of maybe a bad "starter marriage", or a long relationship with a guy who wouldn't commit. You know the sort, the 33 year old "professional saxophone player" who has been with her since she was 23, and has never held down a real job, because "he's an artist, man".

She said no, she'd rarely had relationships over six months long—and that usually the bloke ended it because she didn't want kids. She then said her smug married friends had always been taunting her that she'd change her mind as she got older, and she was enjoying proving them wrong, and watching them get divorced. 

We talked about how the people we'd known at university had aged, got married, had kids, got divorced. I am just entering the phase of the first round of friend's divorces, but my facebook newsfeed if printed out would be pretty much a wedding-baby-wedding-baby montage for about 14 feet. It's got so bad I've recently installed a thing called "Unbaby me" which replaces images of children with images of the Associated Press' best photographs of the day.

This occasionally leads to disasters when I see a friend has posted a photo of a man skydiving into a volcano wreathed with lightning, comment "awesome pic!" and they say "I know! She's just got her third tooth!". The Cougar found this idea hilarious, and I sent her the link to it there and then. We got onto the thin ice territory of why she didn't want kids—she fairly matter-of-factly said she liked the *idea* of children, but thought as someone who'd struggled with anorexia all her life, she'd find it impossible to go through pregnancy. It was something that as a bloke with a healthy (probably too healthy) relationship with food had never occurred to me as a reason not to have kids, but I totally get it.

She really liked me, and we emailed & texted a bit over the next few days. She is a bit put out that I didn't want to "lead her on" and do more romantic dating with her because I want kids. She said something that made me feel very sad, when she said "Good men always want the meat, only dogs get left the bones". We've chatted more since, and agreed that because I wanted kids, and she didn't, it probably wasn't going to work as a romance, but we are on very good terms, and have seen each other since.

She's exactly the sort of woman I could see myself with if I'm single and 50; but, sadly, I'm single and 32. It's just a shame we want different things. What can I say, I'm a sucker for a woman who knows her way around a Leica:)