In The Middle

Dear Emily,
A close friend of mine has been dating this guy for a few months. At first, I was very supportive. He seemed to have the stability her free spirit needed. But as things get more serious between them – I’m starting to see more and more red flags. He seems to take a more parental role in their relationship and it doesn’t seem healthy. She regularly asks me what I think of him and sometimes I’ll lightly give my honest opinion – but I doesn’t really seem to affect her view of him. One one hand, it doesn’t seem like my business to get involved. She’s an adult and can do what she wants. On the other hand, if I were dating a giant red flag in a trench coat – I would want someone to tell me.

Should I Even Be In The Middle

I think there are a few ways to go about this, but you did write that your friend regularly asks you what you think about him. She wants your opinion. If your Light Honest Opinion ™ isn’t prompting a discussion of the concerns you see in their relationship, then go full honest. That’s hard, I know. But as you said, if you were dating someone who a friend had legitimate concerns about, you’d want to know. Tell her that you care about her but that you noticed some red flags and that they worry you.

If you do tell her what you really think, she probably wont like it. There may be a little fallout period, she may get upset. So that’s something to prepare for. You can also just keep doing what you’re doing and see if the red flags become apparent to her on her own. That’s tough but sometimes all we can do is sit back and watch a train wreck happen. She’s in charge of her own life and will make her own mistakes, as we all do.

Delightfully yours,

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