Dating Diary 12: Serial Dating — Easy Online, But Much Harder In Real Life

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In this week’s instalment from High50‘s dating columnist Louisa Whitehead-Payne, Louisa’s flirtations with four potential dates move offline and into real life. Will the reality be as thrilling as the anticipation?

I’m having fortnightly dates with my millionaire, but since he’s sexually reluctant I am also currently working four guys from Encounters. Here they are:

Vice Man: bright and funny, the former vice chancellor of a university. Does fun things like going up in a balloon at the weekend and to the Cropredy Convention festival.

I send him batty texts about country music, cider, my West Country roots and folk music. We spark off each other and I think he is intrigued. We set up a pub dinner date next week. He sounds fun and I am really excited.

Guitar Man: a dodgy start when I accidentally left the ‘a’ off Louisa when I revealed my name. He took a lot of convincing that I was not transvestite.

He’s very nice looking in his pic and seems galvanized by the fact that I am seeing a collection of chaps. Bit of fight in him which I find sexy. We set a lunch date on a Saturday in three weeks’ time.

Brighton Boy: a semi-retired investment banker who comes to London regularly. We had a delightful hour-long chat on the phone. I really like the sound of this guy and we set a date in London for tea next week.

Home Boy: our first phone chat is effortless and long, which bodes well, I think. We have lots to chat about as I grew up in Weston-Super-Mare and he lives nearby in Porlock. Lunch is fixed for a date when I happen to be staying in nearby Bodmin.

The Dates: The Good, The Bad And The Portly

Date 1: Vice Man The pub is in the ass end of nowhere: cold, damp and the food is lousy. Spending the evening freezing and eating prison food is not my idea of a good time. He asks me for a second date and I agree, mostly because I can’t quite separate the bad venue experience from my assessment of him. He is interesting enough to give a second chance to.

Date 2: Brighton Boy We are texting to agree to a venue. He suggests Goring. I can’t get to Surrey that day, I explain. No reply. I send him another text just checking what is going on. No reply. I check again. No reply.

I realize that he must have meant the Goring Hotel, London, not Goring-on-Thames, so I text him saying I have got my Gorings resolved and am looking forward to our tea. No reply.

I get the message, or lack of them. It seems a bit harsh to dismiss a Goring-muddler so brutally, but I send him a gracious text saying I assume he has had second thoughts about meeting up and that I wish him all the best with his search.

No reply. Maybe his wife found his phone.

Date 3: Second Date With Vice Man Much nicer than our freezing first encounter. I like him. He is witty and kind and tells me I am lovely. He was obviously a handsome man at one time, but is a little portly now and, try as I might, I just don’t fancy him.

So when asked for another date, I say with a sigh, “Ah, Vice Man, you are lovely, but not for me”. Kiss on the cheek and off. Lots of texts over the next week to win me round … I reply to all of them, but it really is no dice for Vice.

Date 4: Guitar Man We settle on a pub just outside Swindon. It is shabby chic, with live music, in a pretty village. The weather is gorgeous and I settle in on a sunny, flower-filled terrace.

Ten minutes later, an elderly gentleman in a blazer and chinos approaches me. Dear God, his photo must be 20 years old. Over lunch, he interviews me as if for a prospective wife. Can I cook? Do I have any hobbies? Can I forgive my husband? He is dull and I am bored out of my skull.

Escorting me to my car, he asks to see me again. I say “maybe”… That doesn’t sound good, he says. I agree and put my foot on the gas.

Three down. Last of the batch on Monday.

The cloak of anonymity eliminates good manners with Internet dating. And liking someone on the phone isn’t the same as getting that spark in real life. Unfortunately, you have to let them down in real life, which is tough. So there’s another double-whammy in the brutal world of Internet dating.

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Ten Ways To Have More Sex (Especially If You’re Over 50 And Married)

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Faith Nouri is licensed to practice law in both the U.S. and Canadian Federal Courts. Ms. Nouri is an attorney at law in California, and a Barrister & Solicitor in British Columbia, Canada.