Bestie Danger! 4 Signs His Flirting With Your Friends Is Going Too Far.

Hey there, Steve here and welcome to this week’s private eye post. Whenever we’re called to investigate a possible affair where the man is cheating, about half the time the suspect relationship involves a friend of the woman hiring our services.

These affairs don’t start overnight. They develop over time. Of course, you want your man to get along with your friends. That way, you can all hang out together and have fun, right?

But exactly when does that friendly banter, the “innocent” flirting, become a problem?

Below you’ll find the 4 main signs that you need to be aware of.

Disclaimer: This information is for general educational purposes only and may not apply to all situations — it would be a boring life if we were all the same. For help with an individual situation, please contact us or, when available, use the live chat feature on this page.

#1 The Solo Flirt

It’s easy to pick up if something is going too far when he first meets your friends. You can speak with him and define boundaries if he’s overstepped the mark. But after a while, when you’re deeper into your relationship, he’ll be much more comfortable around your gang. This is the time to take notice of what’s going on. Does he flirt with just one of your friends? Or does he flirt with them all? If it’s just the one, then there may be a good reason to have a chat and rein him in.

#2 Confident or Confidant Flirt

Women typically start affairs by becoming emotionally involved first, then progressing to a physical relationship. But sometimes men do this too — the boundaries of approach have been removed when he’s speaking to your friends. If you find that he’s confiding in one of your besties, and they tell you something you had no clue about, it’s high time to delve deeper. He’s confiding information and it can lead to more emotional intimacy — see the “Emotional Flirt” at #4 below.

#3 Red-Faced Flirt

There’s sometimes a fine line between flirting and cheating. If you discuss his flirting and he becomes shy, awkward, or red-faced, then he must feel like there’s something behind his flirting words and actions. Kind of like he’s been “found out.” A good technique is to probe gently in conversation and watch his reaction.

#4 Emotional Flirt

The “Emotional Flirt” is where his flirting takes a sinister twist, and he starts talking to your besties about emotionally intimate details he should only be sharing with you. This is the precursor to cheating, and you need to stop it happening immediately. Take some time out from the friend in question if you can do it without it being obvious. If you can’t, make sure you’re always a three and never leave the two of them alone.


When it comes to flirting, different couples have different boundaries on what’s acceptable. Talk to your partner before it becomes an issue, and make sure he knows exactly what is and isn’t right for your relationship.

Follow us on Facebook for more information on signs of flirting becoming cheating, and how to get help if you think you need to.

Until next week,