When I was in college, one of my roommates had a boyfriend. He was always very nice to me. My roommate always told me it was because he had a crush on me, but I ignored it. I thought it was because he felt bad for me because I was having such a rough time. He sent me a card in the mail once and if we (his girlfriend, himself, and I) met up for lunch he insisted on paying for the three of us.
So one summer we started e-mailing each other. It was benign. I may have started it asking a computer question. I really can't remember the details. I do remember that in our politeness I asked how his summer was going and he started to be very honest with me and tell me that he was having problems with my roommate.
Naturally I asked if he had talked to my roommate about his feelings and he said that he had. He said that the conversations were going no where and that nothing was changing. I basically gave him the same advice I would give anyone else: you have choices. If you think it's bad, then break up. Don't prolong the agony. This is dating we're talking about. I wouldn't give that kind of advice to married couples.
My roommate transferred schools after that summer. She went and followed her teacher. During that time the boyfriend broke up with her. Miserable she transferred back the following year. She was my roommate again and I had been honest to her and told her about the e-mails. I'm too transparent, I guess. A few weeks past and one night I came back to the dorm and found her sitting on the bed in tears.
"What's wrong?" I asked her. "I need to know the truth. What exactly did you tell him?" So I told her. I told her that I told him to talk to her about the problems with the relationship. She said he never did. Whether he did or not I to this day have no way of knowing. He said he did. She said he didn't. My guess is because he's such a softy he told her in the nicest way possible and she sloughed it off and didn't take it as seriously. I told her that if he was unhappy that he had a decision to make. And I emphasized that I did NOT tell him to break up with her. Which is true. I never explicitly said that. I told him to weigh his options on his own. But I realized then that I was probably getting too dangerously close to saying just that.
You'd think it would end there that I would learn my lesson, but no. Same roommate started dating someone else. We all went to the same school and during my lunch break, I ran into him at lunch and asked if I could join him. "How's it going?" I asked. And then he told me. I told him that if he was miserable that he needed to take it up with her, but not to prolong the agony. If he didn't like her it would only make things worse for her. And I left it alone.
But apparently she found out because after that she was very distrustful of me around anyone she dated.
Around this time I started dating a friend of mine that I'd known since junior high school. He had had an enormous crush on me and now had transferred to my college. Friends suggested that we date. I didn't think it was a good idea because I couldn't figure how I felt about him. After years of him being my friend could he be something more? I decided to give it a shot. Turns out I was right. He was my friend. He was a nice guy. He just wasn't what I was looking for. I'm a city girl. He liked shooting guns, hiking, and wearing shorts....in the winter. He was also very bitter about highschool. And even though we shared issues with highschool I wasn't nearly as angry. He was holding grudges.
So I broke it off. My roommate, in the meantime, really liked him a lot. It was obvious. Suddenly she was sitting next to him in class...and I was on the opposite side of her. She asked me if it would be okay to date him so I gave her my blessing. He's my friend. If she makes him happy go for it.
But then inevitably what happens during the beginning of a romance...you don't see your roommate hardly ever. My mom was dealing with pneumonia and then she was hospitalized. So my friend, who lived in the same town, drove me and her home to the hospital to see my mom. I fretted and worried. And they understood me. We talked about it a lot in the 2 hour or so drive to the hospital.
But then my mom was diagnosed with cancer. I found out while back at school. Seeking solace in a friend I had since junior high or a roommate...well I couldn't find them. I asked if one of them would at least surface because I really needed someone but they, in the throws of love, ignored me. And my roommate had the gall to tell me that I was jealous.
I stopped talking to either one of them. She did eventually call and ask me to come to their wedding. And I told her no. I wanted no part in drama. It was clear that she thought that I couldn't rise above jealousy. And it was partially my fault because I couldn't keep my nose out of it. So I decided it was better that she didn't have me around to ignite suspicion. They are married now with two girls. I wish them well even though from friends I've heard that they've gone a little odd by starting their own church. And I never did see him at the hs reunion. Our mutual friend said that he begged him to come, but he had refused. Apparently he still has grudges.
In the end, I have no regrets other than I had to learn my lesson the hard way: even if you are asked about advice, it's better not to give it in the areas of romance.