Dear Advice Columnist: My Friend's Boyfriend Is Flirting With Me

Should I confront him or stay quiet to save my friendship?

Mar. 31, 2026 at 10:49am

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A reader is seeking advice after her best friend's boyfriend has started making her feel uncomfortable with flirtatious comments and social media activity. The reader is unsure whether to confront the boyfriend directly, tell her friend, or stay quiet to avoid jeopardizing the friendship.

Why it matters

This situation raises difficult questions about loyalty, boundaries, and how to handle inappropriate behavior from a friend's partner without damaging the friendship. Navigating these delicate personal dynamics can be challenging.

The details

The reader states that the boyfriend's behavior started out as just being "nice" but has now crossed into "uncomfortable territory" with comments on her appearance and frequent social media interactions. The reader is worried about how to address the situation without causing major conflict in the friendship.

  • The inappropriate behavior from the boyfriend has been ongoing for an unspecified period of time.

The players

Reader

The person seeking advice about their best friend's boyfriend flirting with them.

Best Friend

The reader's close friend who is in a relationship with the flirtatious boyfriend.

Boyfriend

The friend's partner who has been making the reader feel uncomfortable with flirtatious comments and social media activity.

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What they’re saying

“This is bad. Tricky tricky tricky tricky. Well, if it was me in this situation, I would say something to the gentleman. Okay. Say, you know what, I know you're just flirting a little bit, we're having a good time. But please, it's making me feel uncomfortable.”

— Grandma Gail, Advice Columnist

“Her allegiance is to her friend, not to this guy. So why does why does she care about talking to this guy? Why doesn't she just go to her friend and be like, 'This guy is being weird?'”

— Kim, Advice Columnist

“Yeah, and she very well might be.”

— Grandma Gail, Advice Columnist

The takeaway

This situation highlights the delicate balance between maintaining a friendship and addressing inappropriate behavior from a friend's partner. The advice columnists suggest the reader should have an honest, private conversation with the boyfriend to set clear boundaries, and then decide whether to inform the friend depending on how the boyfriend responds. Prioritizing the friendship while also standing up for one's own comfort is key.