We’ve given you a lot of great advice on what to do in a relationship. But, DateSpacers, we’re realistic – things don’t always work out. So to prepare you for those possibilities, we’re giving you a series on how to break up. Parts I and II can be found here and here, respectively. Your author is H.C. Ingram.

How do you tell your friend when she should break up with someone?

True story: So my uncle has been dating my aunt’s co-worker. The thing is he really likes another woman (a girl, actually…but let’s not go there) and has not been completely honest with my aunt’s co-worker and is frankly acting like a douche. My aunt really likes this woman and was hoping to become better friends but doesn’t know how to say anything. (And before you ask she has told my uncle not to be such a douche to no avail). Clearly the co-worker should walk away but she’d not getting a clue, so what should my aunt do?

So, in this scenario I would have no problem suggesting that she callously rat out my uncle for being a jerk and overall douche (and for repeatedly locking me in closets). But seriously, in most situations, telling a friend her boyfriend is a douche is…tricky.

No one wants to hear “he’s just not that into you” or even “he likes someone else” – not even if it’s true.

People have said that to me when it’s been true (and I knew it) and I still wanted to punch them in the face. Fact: no matter how you say it or how kindly you mean it – telling someone their significant other is a douche will make you sound judgmental and obnoxious.

Tell a story

So if you have to say something – the best way to communicate your advice is anecdotal. The more sincere the better, but structured the right way a story can let your friend come to his/her own (non-judged) conclusions.

For example when I was struggling to get off a roller coaster ride with a recent divorcee: I surveyed friends of mine who had been divorced. They said pretty much the same thing (RUN! Far away!). But, I remember my friend Ben (who recently remarried) saying to me that after his divorce – the first couple years were a complete disaster. I don’t know why but it stuck and made it easier to get off the ride.

Still it’s a tricky thing. With your very very best friends you can be more direct but with most I suspect even the best of us keep our heads low and just try to help with the fall out.

H.C. Ingram is a marketing manager living in exile in Westchester, who appreciates any and every opportunity to hop a train to GCT. Her perfect New York date depends on the company – but might simply be wandering around Central Park and sitting in the sun on warm rocks.