The awkwardness of friendship after dating

Published: May 21, 2012 | Last Updated: May 21, 2012 By | 1 Reply Continue Reading


Hello Dr. Irene,

I really cared a lot about someone whom I dated. After the end of our dating
relationship three years ago, I was devastated. However, I was very willing to
be his friend. For the last two years, I was doing all of the hard work and
effort to maintain this friendship. 

Last year, when I was planning to go to visit another good friend in New York, he
happened to be going there at the same time. I asked him if we could fly back together.
When he told me he really preferred to fly by himself, it felt like a slap in
the face because of all the effort I had put into this friendship. So I walked
away and hadn’t talked to him for a year. 

Last week, I bumped into him unexpectedly on
evening at a social event when I was spending time with my close friends. It
was awkward yet a surprise. I extended my hand to shake his, however he
transgressed my boundaries by hugging me. I was being nice and respectful even
though I did not really like him anymore. He introduced me to his new boyfriend
as his friend. I wanted to tell him face to face that we were not friends at
all any more but decided to save him this embarrassment in front of his new


Should I just simply make it clear to him by
sending him an email that we actually have nothing in common and that I am not
his friend? Or just continue to do my own stuff and not making any contacts to

Signed, Darren



Hi Darren,

It’s hard to make the
transition from dating someone to being "just friends"—especially when one
person wants more from the relationship than the other. The transition couldn’t
have been an easy one for either of you.


When your friend turned down
your request to fly back from New York together, he clearly signaled that he wanted to
make a clean break. I’m sure it was difficult for you to accept that he no
longer valued even the remaining vestiges of your friendship.


My guess is that he didn’t
want to embarrass you, himself, or others at the social event—either by
ignoring you or going into the details of your prior relationship. People often
use the term "friend" quite loosely; it includes people who are more distant
acquaintances. My sense is that his hug was pretty perfunctory, too.


I understand how it might
sting to bump into him with another boyfriend. Even though you had moved on,
finding yourself in a situation like the one you describe can open old wounds. I’m glad you didn’t react
instinctively and, instead, are thinking about whether to respond to him.


opinion: There’s no reason to contact him again. It sounds like this
relationship is over for both of you. He’s certainly moved on and has shown
no interest in maintaining a relationship with you. Hopefully, you won’t bump into him again—or will feel the hurt less intensely if you do.

Hope this helps.

My best, Irene





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  1. Anonymous says:

    me and my best friend have been best friends for the longest time but i feel like i’m being forced to leave her because of a pointless fight that i don’t even remember why it happened. all i remember is that we fought in the locker room in gym and it went all the way out of the locker room and into the gym. we fought until she went and told the gym teacher and then told the guidance counselor and that was the last time i spoke top her. my mom found out soon after that and is now on my constant watch so then i wont talk to her. she is forcing me to remove my best friend from my life and its making me depressed.. i never wanted to have to let her go but i’m forced not to talk her. worst of all if my mom finds out that i’ve made any contact with her shes gonna tell my friends mother and tell her to make my friend stay away from me. i don’t know what else to do. what should i do?

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