Consult your friend first
Before you go sticking your tongue in stray orifices (like her face, ya pervert) talk to your friend and tell him how you feel. Take solace in the fact that there's no conceivable way it can not be awkward.
"Directly!" chimes in the good doc. "Ask directly, say the words. Inferring, by definition, leaves room for interpretation. Even if it may be uncomfortable, make your desires and intentions known. Though this might not solve everything, it's a good first step."
Objectively, it's a weird thing to go after someone who definitely had sex with your best friend. Eskimo brother be damned! Wait, is it still kosher to use the term "Eskimo"? Wait, is it still kosher to use the term "kosher" when not talking about food blessed by a rabbi?!
Think of the conversation as a PowerPoint presentation. Walk them through your feelings, explain your intentions, and really try to convey that you're not just looking for sex and legitimately can fall in love. Still... tread very, very lightly and acknowledge that what you're doing is a huge social faux pas.
Follow your friend's advice closely
So, maybe your friend is kinda cool with it, but has some reservations. Whatever you do, do not ignore those reservations. If he’s over her, but will need a few months to be fine with the concept of you two as a couple, try your hardest to give him space.
If seeing you two kiss or show affection is going to give him some kind of mental breakdown, figure out a plan to make it work -- pending he gives the OK for you two to date.
Don't flaunt your love
Even if your friend claims to not care about witnessing affection, make a point to tone it down while around him. There's nothing wrong with holding hands or kissing, but reconsider going into a full-on dry-hump session while you're all sitting on the couch together watching Waterworld.
Don't go behind their back
We're saving the best for last, except this one is "best" in the sense that it’s the best way you’ll get excommunicated by your group of friends forever if you do it. Don't mess around with your friend's ex behind his back. That's a shitty thing to do and they will almost always, inevitably, find out.
"This is the only answer that's simple," says Dr. Tibbals. "No. Never."
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Jeremy Glass is a writer for Thrillist and has finally learned his lesson.