January 6th, 2011
Okay so you seem like someone who may know how to handle this or at least be able to give a rational female point of view on it. I genuinely can't talk to real-life friends about it because they all know at least one of the two parties involved. It's a two part dilemma that I'm not exactly sure how to handle like a grown up. I have mastered the teenage failure scenario but this is a little trickier.
Part I: How exactly does one tell their best friend that you like his exgirlfriend?
Part II: Assuming you live past Part I, how does a guy, HYPOTHETICALLY of course, then tell the girl or is it even as simple as "telling" her? As you can tell even by the phrasing, this isn't my strong suit.
Any help at all, massively appreciated, seriously.
Thanks,
A.
digitalfaun

Well, let me first preface this by telling you I have little experience in this exact scenario. However, based on my limited experiences, I will try and tell you how I would navigate these dangerous water.

I would flip flop the scenario. Find out if the girl has any interest in you. In all honesty she may have no attraction to you at all, I am sorry if that is blunt, but by finding out her intentions you may or may not find out if it is even worth persuing.

Now, mentioning this to the best friend. Wow. It all depends on the scenario, how long did they date? Was it an amicable break up? You need to figure out the details. If he/she has moved on, but still has some resentment or feelings it gets even tougher. If it was a casual sort of thing, it may be easier.

Here are my main rules for relationships/friendships:

1. Be honest.

2. Don’t be unrealistic about expectations from others.

3. Be realistic with yourself.

4. Ask yourself how you’d handle hearing or doing something before you say or do it to the person in your life.

5. Fight for what you want, and fight against what you don’t want.

I hope this helped. Let me know the specifics and I will be honest with you as to what I would do.

5 notes
  1. suitsandboots said: I don’t mean to be negative but if you are willing to pursue this girl, you need to also be willing to sacrifice the relationship with your best friend. I sincerely doubt you can have both without issue.
  2. thatkindofwoman posted this
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