A little background info first. I have been in love with my best friend for 3 years. I know it could never work because of the long distance, but the feelings are still there. A good friend of mine who is an old acquaintance of my best friend, just got back in touch with him and wants to date him. She keeps asking me if it’s okay with me and I lie and tell her yes. She says she doesn’t want to ruin our friendship. I want them both to be happy, but at the same time I almost feel betrayed. My best friend is the type of guy that you have to come right out and say you’re interested in him otherwise he’ll never pick up the signals. She wants me to tell him that she likes him (yes its very junior high). What should I do? I want them both to be happy, but I’m afraid that things will be awkward between all of us. Help Adri!
–Stuck In the Middle

I was in a similar position back in high school. I really liked K, but he liked E, and she liked him too. And they were both my good friends. So what happened? I didn’t say anything, introduced them, they dated, I was miserable for five months. Not only was I miserable, but I also really grew bitter and upset at my two best friends, especially when I saw how happy they were. Eventually, I ended up saying some snarky things which helped lead to their breakup. I came clean after a while, E and I aren’t good friends anymore. And then I dated K for a few months and broke up because the situation had gotten too weird. So, based on the outcome of that situation here’s my advice:

Be as honest as you can to your girl-friend. Maybe you’re not prepared to tell your BFF, and that’s okay. But explain to her that you feel uncomfortable playing match-maker. Tell her that you’re not sure what your feelings are toward him, but that you think that playing match-maker isn’t up your alley. Especially because if you introduce them, in a lot of cases, you will somehow become one or both’s confidants, and that’s puts you in a weird position. Make it clear that you don’t want to be involved. Or be totally honest with your girl-friend. Tell her that you really like your BFF, but haven’t found the guts/way to tell him and that you’d rather step outside of this. Because, trust me, no good will come of you facilitating your own bitterness and resentment. Unless you’re a really good doormat.