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'Penny might suit a sergeant major, but she'd probably try to organise him too...' Watch what happened when we played Cilla...

By Ursula Hirschkorn for MailOnline
Updated: 08:22 EST, 21 May 2010

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Two singletons, three dates over three weeks, one aim - to see if they're a match made in heaven. Meet this week's potential soul mates...

Name: Nick Thomas-Webster

Age: 58

Location: Bournemouth, Dorset

Occupation: Legal consultant

Relationship history: Single for nine years after splitting from his ex-partner. He has six children.

Ideal woman: Keira Knightley

Name: Penny Doran

Age: 56

Location: Camberley, Surrey

Occupation: Tour leader

Relationship history: Never married, single for one year after breaking up with boyfriend.

Ideal man: Rafael Nadal

DATE ONE: A stroll around a stately home

Nick: Penny came across as quite confident. She told me she works as a tour leader, and it's obvious she is used to being in command as she tends to try to run everything. She is not the sort of woman I'd normally go for as I'm 6ft 4in and she's around 5ft, so there's quite a height discrepancy.

I went into the date with an open mind but I found myself just listening to what Penny had to say - she didn't ask me anything about myself. But she's a pleasant girl, so we'll have to see how the next date goes.

Penny may be small, but she's definitely in charge

Penny: When Nick stood up to greet me as I arrived, the height difference was hilarious. I think that might have put him off a bit - I mean, I'd have to stand on a stool if we wanted to kiss.

I found Nick nice and chatty. But after lunch we went for a walk in the grounds of the house and there were two options: a long walk or a short one. I would have been happy to go on the long walk to spend more time with him, but he said he only wanted to do the short one, so perhaps I like him more than he likes me.

DATE TWO: Karting for beginners

Lewis Hamilton? He's no match for this pair

Nick: Just like on our last date, Penny started organising everyone. The only time she was quiet was when they were telling us how to drive the karts, and I think that's only because she was frightened because she doesn't drive. Because she was a bit nervous, I told her to follow me so that I could help her find the 'racing lines' to follow through the bends. She did two laps like that, but then said she wanted to do it her way.

Penny is pleasant, but wearing, company. Spending an afternoon with her would be okay, but I don't think I could date her on a long-term basis - she's a bit too much for me to handle

Penny: The date was absolutely fabulous. Even though I am a nondriver, I got a huge adrenaline rush out of thundering around the track. I felt like Michael Schumacher - even though I am so short that they had to give me a child's kart.

I was more relaxed with Nick on this date, but I have no idea how he feels about me. He kissed me on the cheek when we said goodbye, but I am just not picking up any vibes from him. I don't know if there will be any romance between us, but either way I'd like to stay friends with Nick.

DATE THREE: An art gallery tour

Was their final date like watching paint dry?

Nick: With a relationship, sometimes you have to adapt to make things work, but I think Penny's too set in her ways to change. She might suit a sergeant major, but she'd probably try to organise him, too. I couldn't tell whether she's interested in me, and as I'm not that interested in her, it's best for us both to move on.

Penny: Nick is lovely, but we agreed the distance between us was too far for us to have a relationship. I think it bothered him more than me, though. I believe if two people are meant to be together, distance should be nothing.

I think I have a lot to offer. I'm sporty, I love to dance and travel, but Nick wasn't that interested in asking me about myself. He seemed in a hurry to get away, which was a shame as it was a lovely day. I ended up exploring Southampton on my own.

The Vyne, Sherborne St John, tel: 01256 883858, www.nationaltrust.org.uk; Team Sport Camberley, tel: 08444 109109, www.team-sport.co.uk; Buon Gusto, Southampton, tel: 02380 331543, www.buon-gusto.co.uk; Southampton City Art Gallery, tel: 023 8083 2277, www.southampton.gov.uk/s-leisure

Looking for love? Send a profile of yourself, in no more than 50 words, plus a photo, to dating@weekend.co.uk, then keep your fingers crossed...

Next week: Will our daters' passions be inflamed at a samba-dancing show?