I’m in a tabletop roleplaying group with three other people; the DM (Dungeon Master) and another guy are old friends of mine, while the third one is a newcomer to the group. 

The DM is having a big birthday party and invites all of us; [Old Friend’s Fiancée] and his sister are also friends of the DM’s, so they’re invited too. [Old Friend], [Fiancée], and [Sister] arrive together.

Every time [Newcomer] is in Fiancée’s orbit, whether [Old Friend] is there or not, he starts flirting with her. He’s not being aggressive or rude, but he’s clearly trying to impress her. She’s a very polite person, and I think [Old Friend] finds it more funny than anything, so neither of them shuts him down entirely, but I’m baffled at why this guy thinks he has a shot with a woman who’s engaged, especially right in front of her partner.

Finally, he and I are in the kitchen with no one else around.

Me: “Dude, why do you keep hitting on [Fiancée]?”

Newcomer: “What? I’m not!”

Me: “Yes, you are.”

Newcomer: “I’ve barely talked to [Fiancée].”

Me: “You’ve been talking to her non-stop!”

Newcomer: “No, I’ve been talking to [Sister].”

Me: “…the one wearing the green shirt?”

Newcomer: “Yeah, of course.”

Me: “[Newcomer]. That is not [Sister]. That is [Fiancée].”

Newcomer: “What? No way!”

Now, at this point, if he’d said the confusion was because [Old Friend] and [Fiancée] look more alike (both have blue eyes and dark hair, while [Sister] has hazel eyes and dyes her hair red), or even just that he’d just gotten them mixed up when they came in together, I would chalk it up to a humourous misunderstanding. Instead, he comes out with:

Newcomer: “But she’s really hot! I assumed she was his sister and the other one was his fiancée because there’s no way he could pull someone like her. [Sister] is definitely more in his league.”

Me: “…Are you saying he should be marrying his sister?”

Newcomer: “No, just that it would make more sense for him to be with someone with looks like hers, you know, not a pretty girl.”

Bear in mind, this guy isn’t exactly winning any beauty contests himself, and as should be obvious, he’s not oozing with charm, either. It’s one thing to have an opinion about someone’s looks, and another to just casually say that you think two people are unattractive and thus unworthy of being with an attractive person. 

Unsurprisingly, more unappealing things about him came out over time, and he was not invited to play in our next campaign or to any more parties.

I’m an eighteen-year-old waitress. I had this couple sit in my section. It was later at night (almost 8 PM) when I started serving them. The whole time I was serving them, it seemed to be going well. I got them their drinks, they ordered, I brought out their food, and I checked up on them, and everything was fine. They seemed to be slowing down, so I asked if they were still doing okay, and the guy asked for a box and the check. Cool. I brought those to them.

I circled back around to find the wife with her hand up, holding the check and her card in the air. Not waving it, just sitting there lol. The husband was in the bathroom, so it was just her at the table. 

I walked up and took their plates, and I asked if she was ready for me to run the card. She said:

Wife: “Oh, you’re paying attention to me now that my husband isn’t here.”

And she handed me her card. I laughed because I thought she was joking and walked away. Then I thought about it and was like… is she implying that I’m flirting with her husband? 

I dropped off her card and said to have a goodnight. She said something under her breath and shook her head.

Oh yeah, she definitely thought I was flirting with her husband, and I couldn’t understand why. As a server, I have always made it a point to divide my attention equally to all the customers at my tables.

They weren’t the type of table that was joking or bantering with me or anything. The husband was the one who spoke up about needing boxes or a refill, but nothing beyond that. And again, I’m young, and I’m not an outgoing person, and I most certainly do not have a flirty personality either.

So, again, I had no idea where she was getting any flirty vibes. Another thing to note: the guy seemed significantly younger than the wife. The guy looked like he was in his twenties and she looked to be in her late thirties. Clearly this was coming from a place of insecurity. 

She tipped me $4.51 on $33.48 (before tax, $36.49 after tax), so from then on out, for a while after that, whenever I would get a table with a couple, I would make sure to make eye contact with the girl more than the guy because I was so scared of possibly giving off a flirty impression again! Every time I serve a table, I’m overly aware of the amount of eye contact I make; she forever scarred me. 

A few weeks later, they came back in and were at the same exact table they were at last time. And I had to serve them. Again. 

You bet I made sure to acknowledge her and make sure there was no flirtatious vibe at all. They were nice, and she paid and left me a little over 20%, if not 20% exactly, on the bill. I don’t know if she remembered me or not, but I guess I redeemed myself!

Thursday night, it wasn’t going to be that busy. My spot over-staffs the place to death, and I had a s*** section. So, I had the mindset that I was going to make more money than anyone that night. A game.

Last call for happy hour, every drink was an up-sell, I took every table offered to me, regardless of the distance from my section. I was remembering names. My tips that night were 40-50% from a lot of these guests.

My last table was two dudes playing pool. When one started to flirt (in an atrocious way), while I didn’t flirt back, I thought, “This could be my best tip yet.”

He kept asking for my number. This man could have been my father. I told him gently:

Me: “I don’t give my number out at work.”

After he continued, I handed him a pen and said:

Me: “You can give me yours.”

This way, he doesn’t feel rejected, and I could just throw it in the trash. I slip it in my apron and carry on with my closing duties.

Prince Charming offers to pay for his friend as well, and thinking he’s trying to flex, I leave him with the handheld POS to input the gratuity.

He reminds me to call him, and they leave.

17%. My lowest tip at that restaurant as a whole.

The other servers and I were laughing at how much of a loser he is, and I joked about texting him, “Was there something wrong with your service today?” They thought it would be so funny, and so I did, immediately realizing my mistake as now he knew my number.

Sure enough, the FaceTime calls start rolling in. He wants me to come get cash from him as a proper tip. Of course, I would never do this. He claims he’s fallen in love, love at first sight. He’s head over heels.

Oh boy. I tell him I’m not interested, and to have a nice life, and I block.

Well, the next day, I got a phone call. It’s his mother.

She thought I would be at work. Her son had brought her there to meet me. His MOTHER. Said I was the one. But I needed mom’s approval first.

This is a new one for me, guys.

Back in high school, a classmate and very close friend of mine had a big crush on a girl we often met on our way to the bus stop. We knew she had a boyfriend, but nevertheless, my friend wanted to try hitting on her. The problem was that both he and I were absolute beginners with the art of flirting, and it never went past him talking about how beautiful she was.

Until he went on vacation with another classmate and came back all proud of having done his move: he had sent her an anonymous postcard with a declaration.

A few days went by, and the post service delivered the postcard, after which we heard through friends of friends that she had received an anonymous postcard and was fuming about its contents, and that if she could find who had sent it, it would be their end.

I asked my friend what he had written. He told me that to get the courage to write it, he and the other friend had drunk some beer, and then the other friend came up with the awesome declaration: “Your hair is so long and beautiful that I always wondered if it’s fake.”

It didn’t take much to realise that the other friend was also a total novice.

At my gym, there’s a larger guy (that’s how he describes himself) who has been working his a** off to get in shape. He’s awesome and really putting in that work. His wife actually works there at the front desk. They’re a really cute couple, and it’s obvious just from observing their interactions that they’re over the moon for each other. 

Plenty of guys come in and decide to flirt with the front desk woman. She shuts them down all the time, but occasionally these morons decide to mock her husband, not knowing their relationship, to make themselves seem better by comparison.

I witness one such attempt:

Customer: “Ugh, why do some guys even bother. I mean, look how fat that guy is.”

Front Desk Worker: “It’s not surprising. Every time we do it, I let him lick chocolate sauce off me.”

The customer just freezes up, not knowing what to say or do next.

Front Desk Worker: *Calmly.* “Was there anything I could help you with?”

That guy just sheepishly disappeared back into the free weights section, and I was just glad I wasn’t in the middle of a set myself as I was laughing my a** off.