Woman Says a Man Asked Her Out — Then Flirted With Her Friend in the Same Group Chat Two Days Later

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A 38-year-old woman says she was willing to give a man a chance after meeting him at an event, but his behavior before their first real date made her uncomfortable enough to cancel the whole thing.

She explained in a Reddit post that she met a 45-year-old man she called “Paul” through a shared community where different people organize events. They seemed to connect when they met in person. He asked for her number, and she gave it to him.

So far, nothing seemed especially strange.

But they were also in a group chat connected to that community. Not long after getting her number, Paul asked for her friend’s number too. The woman noticed right away because he used almost the exact same wording with the friend that he had used with her.

That bothered her, but she tried to handle it lightly.

Instead of starting a big confrontation, she made a joke about it. That was her way of calling out the overlap without making things immediately tense. She knew they were not a couple. They had not even gone on a proper date yet. But it still felt awkward to watch him repeat the same approach with her friend in a shared space where everyone could see it.

Then Paul asked her on an actual date.

The woman said he had been saying the right things, so she agreed. At that point, she was still open to seeing where it went. She did not expect exclusivity before a first date, and she said clearly that she did not have a problem with him seeing or talking to other women since they were not together.

But two days later, he started aggressively flirting with that same friend in the group chat.

This was not subtle enough for her to ignore. She described it as overly direct, and the fact that it happened in front of her made it feel worse. He knew the two women were friends. He knew they were both in the chat. He had asked one of them on a date and was openly flirting with the other in the same shared space before the date even happened.

That was what made her start to question his motives.

She said it felt like he might be trying to pit them against each other for fun. Maybe that was not his intention. Maybe he truly saw it as harmless flirting before any commitment existed. But from her side, it felt disrespectful and strangely performative, almost like he wanted an audience.

In the comments, she later clarified that she is not into casual dating and had told him she was looking for something serious. She believed he had also said he wanted something serious. That made the group-chat flirting feel even more mismatched with what he had presented to her privately.

It was not jealousy in the way people sometimes use that word to dismiss someone’s discomfort. She was not claiming ownership over him. She was asking whether it made sense to go on a date with someone who was already making her feel embarrassed and uncomfortable before they had even sat down together one-on-one.

That is the thing about early dating: you are not only watching how someone treats you directly. You are also watching how they move through other people. If someone says the right things privately but acts careless publicly, that contrast matters.

The woman seemed to know she could technically still go on the date. She could pretend the flirting was no big deal, remind herself they were not exclusive, and give him a chance to explain. But the whole thing felt off to her.

Commenters were split in tone, though many told her she did not need to force herself into a date she no longer wanted. One person said if his behavior made her feel bad, she could cut him loose early and listen to her gut. That seemed to be the advice that landed.

The woman later said she canceled the date and felt much better afterward.

By the end, the issue was not whether Paul had broken some official dating rule. The issue was that he showed her a version of himself she did not like before the date even happened. And once she saw it, she did not want to ignore it just to prove she was “cool” enough not to care.

Commenters had mixed reactions, but many told her she was not wrong to back out. The strongest support came from people who said early dating is exactly when you are supposed to notice behavior that does not sit right and act on it.

Several commenters said he technically had the right to flirt with other people because they were not exclusive. But others said that did not mean she had to like it, especially because he was doing it with her friend in the same group chat after asking her out.

A lot of people agreed with her that the public nature of it was the problem. If he wanted to keep his options open, he could do that without making it weird in front of the woman he had just asked on a date.

Some commenters told her she was overreacting if she expected commitment before a first date. But even those comments often acknowledged that she could still decide the behavior was not for her.

The most practical advice was to trust the discomfort. Nobody needed to be the villain. She did not owe him a date, and he had already given her enough information to decide she was no longer interested.