Should I tell her she’s marrying a terrible person?

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A girl I share some social circles with with just got engaged and I'm not happy for her. I'm terrified.

Her fiancé is, in the kindest words I can stomach, a horrible person. He has been party to numerous affairs, at least once with a married woman. While dating his fiancee, he has cheated on her multiple times. One of the people he cheated with was my former roommate (who was unaware of the other relationship). Even I have had to reject his advances, for which he despises me. Women going to parties he's attended have been afraid to go without a male date for fear of harassment. He is an excellent liar and has made everything from passive-aggressive "jokes" about friends' sexualities, races, and personalities. He is prone to gaslighting and nothing is ever his fault.

This girl is young – under 21 – and has spent most of her adult life on religious service trips. She has little dating experience. They had been dating for no longer than six months when they got engaged. Their wedding date is three months from now. I know I'm a biased observer, but for what it's worth, his body language toward her seems possessive and I never see her without him. I want to tell this girl what I know. I don't want to perpetuate the bystander effect, and it seems nobody has told her yet. But we're not close, and some of what I have learned is secondhand, albeit from a variety of sources. I have no physical evidence. I'm not sure if it's my place and I worry about her reaction – his even more so. Do I just leave it and hope for the best, whatever that may be? Do I make an effort to let her know she can seek me out if she needs support and let that be the end of it? Or do I try and tell her what I know?

– Flying the Red Flag

First, I have to ask about the group of friends that continues to invite this man to social gatherings. He makes people uncomfortable - many people. Why is he still in the inner (or even outer) circle? Who supports this person's presence?

I know it's hard for people to ditch a longtime friend, but it's possible. You can let it be known that you'd rather see the people you care about without this person in the mix.

As far as telling this woman, you're right about all the concerns. It's not helpful to be a bystander, but you don't really know her. Also, you fear his reaction. That's no good.

My advice is to get together with someone who knows her better and ask about how it might be appropriate to intervene. Perhaps a closer friend already has. Maybe you can get a better sense of what it would be like to approach her yourself.

Some will say to mind your own business, and there's a case to be made for that. All paths are messy here; it's more about which one you can live with.

I used to know a couple – a man and woman – and it had been told to me by mutual friends that the guy was constantly cheating. I always wondered why these friends didn't tell the woman. Now the couple is married and I've heard they're happy. Back then I considered pulling her aside to disclose what I knew, but I was young and it felt like it wasn't my business. Who knows if I did (or didn't do) the right thing? In that case, I think it was about the mutual friends also being young and not wanting to mess with the dynamics of their friend group. Some of the people had been in relationships with the man and didn't want to be discovered. Also, maybe a few of them were telling me this stuff because they hoped I'd open my big mouth and make the decision for them.

The situation in your group sounds worse in a number of ways (her age, life experience, etc.). That's why this is the time to ask someone who's closer, someone you know feels the same way, to help you figure this out. Sometimes there's more bravery – and better planning – in numbers. Maybe talking to a mutual friend will also help you figure out ways to get this person out of your lives. Again, you should not have to see this man when you're trying to relax and have a good time.

– Meredith

Readers? Would you make this your business?