oil-water friend problem

In lesser amounts, it's just the natural problem of having widely disparate experiences with two different friends - if you're talking about college fun with one friend and talking about past parties with two friend, it's awkward.

I was desperately in love with Laura. I started by detesting her three years before, because she was cool, and I was not.
I was in love with her now precisely for the same reason. But I was not artistic enough for her (subsequently she went and married a robotics engineer, of all people ...).

I like a lot my buddy Marco. He is an engineer, and a good one. A thoroughly square dude, honest, clear headed, absolutely reliable. A loyal granitic friend.

I brought them together years ago for a cup of tea. Disaster. They would not speak to each other. I wanted to die, to curl up under the sofa. I tried jokes, and they failed.

That was when I realized that I am a highly customizable person; I adapt myself to my social environment. All is fine, while I am alone. But I have gotten wiser, now I do not try to mix water and oil, no matter how sweet the water or perfumed the oil.