how do you decide when to break up?

I do not think that there is an easy answer to this
question. Before attempting to provide one, I think it is important to
highlight the two ideas contained in the prompt. First, why is it okay to break up with someone. Second, at what time is it okay to break up with
someone. I believe that one may reach a satisfactory answer – or as close as is
likely possible – by attempting to resolve those reasons and doing so at an
appropriate time.

I must further preface my comments by presuming that one
reads this advice out of good faith and not because you have found someone new
on Tinder, you are cheating on them and can no longer bear the guilt, or you want
to get back with your ex.

Reasons

It would be impossible to address the numerous reasons
why someone would want to end a relationship and cast judgment as to whether
they are good or not. However, before throwing in the towel, I think it is
absolutely critical that one put in a genuine effort to resolve the problem. Feel
like there are no shared interests? Suggest some new activities to try on a
weekend or create an alternating schedule of things to do. Think that they have
some annoying habits? Discuss how it makes you feel and work with them to try
and reduce their frequency. Wish they would support you more? Talk about how
their opinions are important to you and how you want a bit more encouragement.

After having a genuine discussion, it is then critical to
realize two things. First, people do not change overnight. If their annoying
habit is that they do not throw their laundry in the hamper, I suspect it would
be an overreaction to storm out of the house with a packed suitcase later that
night after discovering a sock on the bathroom floor. I think it would be
helpful to see change as a process rather than being like flipping a switch.
Assume they care about changing and just need gentle reminders.

Despite this, I will readily admit that some things do
not or cannot change. A serial cheater is not likely to realize the error of
their ways after you catch them for the fifth time. Similarly, people may be
set in their life goals and unwilling to give up their dream of touring the
world – career be damned – while you work your way up the corporate ladder in
New York City. In this latter case, irreconcilable differences and divergent
needs do not necessarily make one party or the other bad people. It is just
something that happens. Your lives intersected at one point and now they no
longer do through no fault of anyone.

Timing

I have encountered a surprising number of people who seem
to exercise terrible judgment as to when it is appropriate to break up. Unless
you are in an abusive relationship or some other similarly dire situation,
announcing your newfound singleness on an anniversary, after their parents have
died, during finals week, or while they are looking for a new job is not a good idea. A breakup could be one
of the worst things to ever happen to a person and it seems to be incredibly
self-centered to relieve your own feelings without regard for what stresses the
other person is going through at the time.

Having said that, I will also concede that there is never
a “good” time to break up with someone. As I said earlier, a breakup could be
one of the worst things to ever happen to a person. However, the reasons that
make you feel as though a breakup is the best choice are not likely to vanish
with time. Part of being an adult is having to make painful choices. You do not
want to be like one man I met who stayed in a four-year relationship with his
boyfriend – even though he wanted to break up with him after the first semester
– because he could never find a “good” time to do so.

When do you decide to break up? Have you made an honest
attempt to resolve whatever problems you think are causing you to want to break
up? Are you following through with your decision at a time when they are not
under any unusual stress? If you can answer the second and third questions in
the affirmative, then I think you will find that the answer to the first
question will be about as good as it is possible to be.

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