Dating Diary Part Two

I’ve got a hot date with a woman who is insanely beautiful — and I suspect a little bit insane … she’s agreed to a date with me after all! So all week I’d been planning our big night out. Cocktails. Dinner. Club. I had it all perfectly arranged and coordinated when she dropped a bombshell on me. “I’ll be bringing my dog with me. Hope that’s OK.” Suddenly, my best laid plans were in ruins. 


My first reaction was ‘What the..? Bring your dog? On a date?’ My second reaction was ‘Where am I going to take this woman and her dog?’ 


I’ve never gone out on a date with a woman and her dog before. I’ve gone out with a woman and her mother, a woman and her best gay friend and a woman and her Rabbi. But never a woman and her dog. 


Why does a woman take her dog out on a first date with a man? Is it for protection? Is she testing me? Is it a case of love me, love my dog? ‘Ok, let’s stay calm’ I told myself. So I asked her what her dog likes to do and she asked, “besides sniffing pavements and barking at other dogs?” 


Now as the date approaches I feel a bit anxious. Before I was worried about trying to impress her. Now I have to impress her and her dog. But how do you impress a dog?  Let’s be honest, her dog is not going to appreciate my witty one-liners, my hilarious anecdotes about famous people I’ve met and you can’t flatter a dog. The only dog orientated conversation I know is, “walkies!”, “good doggie” and “Bloody hell, do I have to clean that up!?”


Anyway, I lied and sent her text saying I LOVE DOGS! Obviously, if she’d said, I’m bringing my pet tarantula I would have said, I LOVE TARANTUALS! When you’re a romancing a woman with a pet, you have to start romancing the pet if you want to win the heart of the woman. I’ve learnt this the hard way. 


I once dated the woman of my dreams – and then I met her cat and our relationship became a nightmare.  Her old, smelly and incontinent cat would pee on our duvet. Her cat would pee on my clothes. Dream girl would say to me, “Isn’t she the most beautiful and wonderful cat in the world?” I would dutifully reply “Absolutely!” Then one day her cat peed on me. So I said to Dream Girl “It’s me or the cat!” And guess who won?


I’ve dated women who have had cats, rabbits, fish, newts and tortoises in their life, but dogs are the most difficult competition a man faces. Dates, boyfriends and husbands come and go – but a woman’s love for her dog is forever. 


I recently heard about a dating show called Puppy Playdate. The show is in production, and the premise is that a girl has a dog and three guys have to take that dog out on a date. After all the dates the dog has to choose which bloke it likes best and then he goes on a date with the girl. The dog even has a wag-o-meter.


I’m bringing my date flowers and special chocolates – but I still haven’t made up my mind what to get the dog.

Cosmo Landesman is the former dating columnist for The Sunday Times and writes about love and romance for a wide range of publications including The Times and The Spectator magazine. He is currently single — but remains optimistic that true love is just one date away. 



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