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.

Some of you who read this will wonder why the hell anyone would need to be told “how to tell if they should break up.” Let me congratulate you, it is nice to be self-aware, bouncing through life in an uncluttered, uncomplicated manner. I’m not suggesting such self-awareness is indicative of a lack depth, merely that it helps. Also you can stop reading now.

For the rest of you, I think you would agree that being in a relationship (inside of love as it were), is a bit like being in a black hole. Ok that’s not true, that would imply super dense gravity and time distortions I think…my geek card doesn’t really give me black hole knowledge privileges. My point is: things seem different when colored by emotions, hormones and the gravity of being in someone else’s orbit. Breaking up is hard especially when considered in conjunction with most people’s tendencies towards the following irrationalities including:

1. Undue weight on sunk costs (remembering the good times)
2. Fear of being /dying alone
3. Fear of the unknown
4. Fear of change

True sometimes it’s easy, like the decision to dump the guy who thought blowjobs weren’t cheating, the guy who never laughed at your jokes or when there is someone much more awesome (it happens). Sometimes though it’s more complicated and listening to your heart feels like prognosticating and we have to look for signs.

The Top 3 Signs

3. Flirting. When a hot guy winks at you or flirts with you do you respond? You know what I mean are you FWI (flirting with intent). People committed or in love do not flirt the same way (don’t play innocent you know what I mean)

2. The friends. Do you like his friends? Do they like you? Personally I think the quality of someone’s friends (and the depth of their relationships) says a lot about them. I also think how well you fit into your partners life says a lot about the long term potential of your affair.
1. How good is the sex? True Story: When one of my friends was contemplating ending it with her live in boyfriend I had to ask , “How’s the Sex?” her answer, “Um.” Ok so maybe you don’t believe bad sex is a deal breaker, but you would be foolish to ignore this important signal your body is sending you.

One final note: breaking up isn’t a necessarily a solo decision. If you both respect the other person, are fairly mature and communicative – you might be surprised that you can figure things out together and sometime things work out even better than you imagined.

Bon courage.

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.

Acknowledgement: Breaking up (from either side) sucks (unless you are a heartless jerk and then you probably won’t read this article anyway).

Breaking up, like an adult requires guts, even more guts than asking someone out because unlike the later there is no positive re-enforcement (e.g. a gratified ego or the possibility of sex) associated with it. Think you can do it? Ok channel your inner Spartan, sack up and read on!

Rip off the band-aid – just do it.

1. Do it in person. Although with the prevalence of technology, one could argue that if the majority of your relationship was conducted over the phone e.g. long distance or some other medium (on-line, IM, texting, etc.) using the same technology to end it is not as taboo as it might been a decade ago. One hard and fast rule – never do it while someone is at work.

2. Be as clear and straightforward as possible. If you are confused don’t break up (I’ll deal with this in a future installment), but if you are sure of how you feel, you aren’t sparing anyone’s feelings by being ambiguous.

3. Articulate your reasons, to an extent. Don’t leave them wondering why you aren’t happy. You can say you don’t think the person is the right person for you. That it won’t work out because of things you may have already discussed (distance, timing, religion etc) don’t mention things they can’t change – perhaps you don’t find them attractive, or their laugh is annoying. (conversely, if you are ever being broken up with, don’t push someone into telling you something you don’t want to hear.)

4. Avoid using cliches. I don’t want to hear – “you deserve more”, “I’m confused”, “I just don’t think I can give you what you need.” Seriously in NYC we’ve all seen it/heard it. If you can’t be original, straightforward and honest will do.

Finally, when in doubt use the golden rule – duh.

Don’t do the following:

Wuss Strategy A – Just Stop Calling Yeah sure eventually s/he will get the picture – and some people like this because it requires minimal effort and it will help the other person get over you quicker because s/he will realize that you are a selfish, immature jerk and you probably don’t keep exes as friends anyway.

Wuss Strategy B – Avoid It… Become emotionally distant, stop doing all the things you were doing when you were still into her/him. Generally make life as unpleasant as possible while you avoid figuring out what you want and if you are lucky s/he will break up with you!

Final Note: Be Prepared
S/He might want to talk/try and talk you out of it. That is going to be painful and generally suck. As best you can, listen, but remain clear about what you want (yeah even if you have awesome break up sex)… and seriously wait at least a few months before trying “to be friends.”

Good luck!

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.