The Dating Game

A couple with shopping bags Illustration: Rex/Shutterstock


All’s fair in love, they say – even if you do have to be a tiny bit sneaky…

“That’s much too soon. No.” Samantha pulled her hand away sharply. “Honestly, David, how many times do I have to tell you?”

I put on my butter-wouldn’t-melt expression. “Sorry. I’m trying, really I am. Can we start again?”

“I need a break,” she pushed back her chair and left the room.

It was our fifth dating lesson and it wasn’t getting any easier.

It all started with a bet. I’d just told my sister about yet another date that had gone wrong before it had even properly started.

Mary had laughed. “Honestly, David, you’re hopeless. Somebody should give you dating lessons.” She glanced over at Samantha. “I bet you could help him.”


“I said my dim brother needs to have dating lessons.”

Samantha shrugged. “Why don’t you teach him? My last relationship ended months ago. You’re the one who’s happily married.”

“I can’t teach him because I’m his sister and it wouldn’t feel right. Plus I’ve been married for so long now, I can’t even remember what dating is like.”

I’d love to help out but…

“Sorry, Mary,” replied Samantha. “I’d love to help out but I have better things to do… like wash my hair and clean out my kitchen cupboards.”

My sister smiled. “Translated that means you don’t know how to do it.”

“Of course I know how. Believe me, if there’s anything that can go wrong on a date, I know about it,” Samantha said with feeling.

“OK,” said Mary. “In that case, I bet you £20 you can’t teach David how to get a second date.”

“Make it £50 and you’re on.”

“Hang on a mo,” I said indignantly. “I’m here, you know. Don’t I get a say?”

“OK, £50,” Mary countered, studiously ignoring me.

Samantha looked me up and down. “He’ll need to work on his appearance for a start… those shoes need to go.” She shook her head, “and that shirt… that colour really doesn’t suit him.” She turned to my sister as though I wasn’t even in the room. “If you give him a makeover first, then I’ll take the bet.”

“It’s a deal,” my sister replied.

“Look here, you two,” I said. “You can’t treat me like this.”

Mary put her arms round me. “Oh, but we can. Admit it David, you’re hopeless at dating. You’ll be thirty five soon. Do you want a girlfriend or not?”

“Yes,” I said cautiously.

“Then we’re all agreed,” said Samantha smugly.

The two women shook hands, and that was that. From that moment, my life ceased to be my own.

On the Saturday, my sister took me shopping for clothes.

“What would you normally buy?” Mary asked me.

I headed to the casualwear section and picked up a white polo shirt.

You need to look smarter, especially on the first couple of dates

She shook her head. “First of all, white isn’t a good idea. It makes you look washed out. Second, you need to look smarter, especially on the first couple of dates. It’s all about first impressions after all.”

She led me to the shirt counter and selected two with thin stripes.

“Won’t they need ironing?”

She frowned at me. “Yes, of course they will.”

“I don’t do ironing.”

She put her hands on her hips and looked straight at me. “Then you’ll just have to start, won’t you?”

I didn’t argue. There wasn’t any point, not when Mary had that look in her eye, the one that said that come hell or high water, she was going to win that bet.

It was a long day. A very long day, but eventually my sister was satisfied.

“Now all we need to do is get your hair tidied up then you’ll be good to go. Which barber do you use?”

“The first one I come to.”

Apparently that wasn’t the right answer. She sighed at me. “You need to go to the same place every time so the hairdresser gets to know your style.”


“Because I say so,” she said.

That Monday evening, I had my first dating lesson with Samantha. I expected it to be at a restaurant – after all, that’s where I usually go on a first date, but Samantha had other ideas.

Come to my place at seven and don’t be late

“A restaurant’s no good. We might need to do things over and over. Come to my place at seven and don’t be late.”

It was a bit of a disaster. It seemed that my handshake was wrong – far too formal – and my smile was too big.

“You look like a serial killer,” Samantha told me more than once.

When I pulled out her chair for her to sit down, that was wrong, too.

“Some women find it patronising,” she explained. So it went on…

fter an hour, she took a leaflet from a drawer. “I don’t know about you, but I’m starving. How about we order a takeaway and try again on Wednesday?”

“Good idea,” I said.

The meal arrived in minutes.

Samantha spread the various boxes across the table and we piled in. Because the lesson was over, it was much easier to relax and we chatted about all kinds of stuff from work. I’m a minion at the same advertising company where Sam works as an administrator.

Another hour went by in a flash and by the time I helped her wash up it was getting late.

“I’d better be going,” I said.

“Same time Wednesday,” she said.

Lesson two was all about when to touch and when not to. Apparently I was getting it all wrong.

“You need to learn how to flirt, to let the woman know that you fancy her. Touch her hand or her arm every now and then, but don’t overdo it.”

It sounded a bit complicated, and sure enough, it was.

Samantha kept sighing at me, saying things like, “It’s been ten minutes and you haven’t touched me at all,” or, “For goodness’ sake, David, not like that – I’m not a cat.”

After a while I asked if we could stop.

“I’m so busy thinking about all the other stuff – listen properly, smile but not too broadly – that I keep forgetting what I’m supposed to do next.”

She stood up and I thought that’s it, lesson over, but luckily she wasn’t that easily beaten.

“Let’s start over,” she said, “only this time, I’ll be you and you be me.” I must have looked blank. “Role play. You’ve done that at work, haven’t you?”

“Yes, lots of times.”

She nodded. “Good. So I’ll play the man and you play the woman. We’re in a restaurant and it’s our first date.”

I’d done some acting in school so it was easier than I’d expected. I noticed that Samantha was making a lot of eye contact, something I wasn’t used to.

I looked away, and she reached out and put her hand on my arm. “I’m having a great time,” she said.

“Really? Because I’m not sure that this is working.”

She let out a huge sigh. “I didn’t mean I’m having a wonderful time teaching you dating skills. It’s what I’d say if I was a man on a first date. Something like that helps the woman to relax.”

“Oh, sorry. I see what you’re doing now.” I tried to get back into my role. “Me too,” I said ever so coyly.

She took my hand and squeezed it, gently. “Do you know what you’d like to order or shall I choose for both of us?”

Surely that’s a bit patronising?

“Hang on a minute,” I said. “Surely that’s a bit patronising? This is the twenty-first century.”

I expected to score some points – after all, that’s what she’d said earlier when I’d pulled out her chair. Instead, it earned me another sigh.

“Honestly, David. Don’t you know anything? Think about it for a moment. This is a first date, maybe in a posh restaurant. The woman’s going to be feeling anxious, so letting the man make the decisions means she can relax. If she doesn’t like what he orders, it’s not her fault.”

For the next five minutes she explains more about the woman’s side of things and I can see she knows her stuff. Not for the first time, I wonder why she’s not in a relationship herself.

“It’s mostly common sense when you think about it. So, shall we continue?” she asked me.

“I’d rather not. I’ve had enough for one night. You’ve given me a lot to think about. I’ll be better next time,” I promised.

Only I wasn’t better the next time or the time after that. If anything, I got worse, and on our sixth lesson, Samantha lost patience with me.

“OK, I give up! I can’t teach you. You’re impossible.”

She took £50 from her purse and put it down on the table.

“It’s OK,” I said. “You don’t have to pay. The bet isn’t valid. I’ve been getting things wrong on purpose.”

“I have no idea what you mean.”

“I mean I wanted the lessons to go on as long as possible.”

She stared as if I was crazy. “Why?”

This was it – crunch time.

“Because I knew that if I asked you out you’d say no… I’m not your type, I’m not six feet four with a six pack, I don’t wear designer clothes… I’m just me, but I wanted to spend time with you – without my sister there.”

Samantha looked shocked. “So Mary doesn’t know about this?”

“She hasn’t a clue. The lessons were her idea, but she thinks I’m just a really bad student.”

For a moment, I thought Samantha might storm off, but then she saw the funny side and started to laugh. In fact she laughed so much she couldn’t speak.

I fetched her a glass of water and she took a sip.

“Thanks,” she managed at last. “You’re right. If you had asked me out, I would have said no. Why would I go out a man whose nickname is One-Date-David? Did you know that’s what they call you at work?”

I nodded and pushed the money back across the table. “I’m sorry. It was a bad idea.”

“Oh no,” she said. “You’re not getting away with that. There’s still one more lesson I need to teach you.”

There. I’ve said it. I guess that’s another big mistake

It was my turn to laugh. “I don’t need lessons. The reason I never get to a second date is because you’re the only woman I’m actually interested in.” I sat back in my chair. “There. I’ve said it. I guess that’s another big mistake, confessing I have feelings too soon.”

She reached across the table and took my hand. “It’s only a mistake if the girl doesn’t feel the same way.”

It’s a cliché, but as we looked into each other’s eyes, I swear the world stopped revolving. I could see in her face that she meant what she said. She’d fallen for me, exactly as I’d hoped. My idiotic idea had actually worked!

“When did this happen?” I asked her.

She grinned. “After lesson one, when we shared that takeaway meal. Right,” she said, suddenly business-like again. “Time for lesson number seven.”

I hadn’t a clue what she meant. “I thought the lessons were over.”

Samantha pouted, and pretended to be hurt. “Lesson seven is one of my favourites. It’s about kissing,” she said, “But if you’d rather not bother…”

I drew her gently towards me and as our lips met, I knew two things for certain: the dating lessons had done the trick, and better still, One-Date-David had gone, never to return.

Look our for more romantic dating stories throughout February…

Karen Byrom

My coffee mug says "professional bookworm" which sums me up really! As commissioning fiction editor on the magazine, I love sharing my reading experience of the latest books, debut authors and more with you all, and would like to hear from you about your favourite books and authors! Email me