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Dating & relationship advice from Kate and Jason.

Aaron Embry… Guest Boyfriend?

Hello Everyone~!

I ran across my old friend Jim yesterday at the mall. We are still the best of friends although there was a time when that friendship was tested almost to the limits.  That was when, for a very short time, I fell for his ex.  Though Jim had parted with Lynn six months before I made my move, there were still lots of awkwardness to say the least.  Good thing I cleared everything with Jim before making my move.  That thoughtfulness may have saved our friendship.  Well that was five years ago, but there are times when I still feel a bit awkward around Jim.

Aaron Embry once said that we can never dictate our hearts who to fall in love with. After all, the ‘heart has reasons that reason itself does not know’. But what if you fall in love with the person that your bestest buddy ever once fell in love with? What basic etiquettes apply when you fall for your best friend’s former girl? Should you let love rule over you or should the bro come before the lady?

Pros vs Cons of Falling for Your Best Friend’s Girl

So while technically she is single and unattached, given that she’s your best buddy’s ‘ex’, the fact still remains that she once dated him and that they will always have a connection that all former lovers have. And that’s what brings all the awkwardness in the world! (Or in your world at least).

And the awkward, I mean, really really awkward part is just the beginning of it. There will always be a question about how your best friend is likely to take it and whether you can give up one for the other. Not to mention, you’re going to get some awkward and telling conversations with the rest of your circle of friends.

Maybe, too, you cannot help but question the intention of the ‘ex’ as far as sincerity is concerned. Is she dating you because she wants to really date you, or is she simply using you to to get back at her ex aka your best friend?

In this complicated dating situation, it would literally be easier to find the proverbial needle in the haystack than to see a good reason to proceed. Testing your best friendship, maybe?

If you’ve got time, here are some online dating tips every man must know (courtesy of You may want to also read this article from Huffington :)

What to Do When You Are in This Situation

Should you find yourself in this very awkward situation, might as well do it the right way and try to do as little damage as possible – to your friendship, to your date, and to yourself most importantly. Here are some tips:

Ask your best friend’s opinion and permission on the matter. In the name of great friendship and civility, you have to take this extra step. Don’t be the guy who stabs his best friend in the back. Even when they are technically not together, you have a moral obligation to do so simply because they did have a relationship, [16] and you are supposed to be best friends.

Figure out her intentions. Is she really interested in you or is she just doing it to spite your buddy? You have to be really careful and conscious about this part simply because (1) you don’t want to be duped, and (2) you don’t want to be the accomplice to a crime towards your best, best buddy!

Avoid mentioning the ex to your best friend and vice versa. Not until you guys have totally gone past the awkward stage can you put the two in the same sentence. Same rule applies to when you have to ask both of them to be in the same room!

Yes, it sure is challenging so better think more than twice before getting into this messy, sticky situation! (And she had better be worth it!)

Perhaps you have more dating and relationships questions?  Buy our book: “We Are Each Other: The Kate & Jason’s Guide To Everlasting Love”; go here:

Posted on 22nd January 2013 in Dating  •  Comments are off for this post

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