This letter is juicy. Good for a Friday.
I am a female in my 20s who needs direction in my relationship with my friend, let's call him Ryan. Ryan and I have known each other for 10 years and throughout that time have been through a lot together. We dated briefly in the beginning of our relationship but I ended up deciding to have a relationship with someone else, and unbeknownst to me at the time broke Ryan's heart. I later found out he was in love with me. We fought due to his anger but made up and remained close. I stayed in my relationship for 3 years while he dated another girl for 2.5 years as well. Both of our relationships had their problems and ended within a few weeks of each other. We became just as close as we used to be and developed a sexual relationship as well. Before I continue, I have to point out, Ryan has a bit of a problem. He did not remain faithful to his girlfriend of 2.5 years. There is something about him that causes girls to literally throw themselves at him so he is constantly "hooking up" with other girls. These girls are always quick flings he has no feelings for. Over the next year of our relationship I began fall in love with Ryan. We continued to spend all of our time together and essentially were in a non-monogamous relationship without the title. I was just "going with the flow" without addressing any feelings we had for each other because it's just something we never do. We literally tell each other EVERYTHING without holding anything back but we NEVER talk about our feelings for each other. We haven't since that time 4 years earlier. Since he continued to have his flings, I knew that he was not ready to settle down and I kept my options open as well even though I wanted to be with him. I went on dates with a couple guys but then I began seeing someone else and I could tell it was different. Ryan had also begun seeing someone and I told him I wanted to give my relationship a try. He asked "What about us?" and I was shocked because I didn't think he wanted anything more then what we had. I asked at the time if I ended things with my new guy if it would change anything and he said not to end it because he couldn't promise me it would. Fast forward and Ryan had a relationship with the woman he was seeing that did not work after a year or so. I ended up falling in love with and marrying the man I was seeing. After 4.5 years of being together he turned our not to be a nice guy and our marriage ended. I was heart broken but am climbing through the rubble and that is not the point of this letter ... Throughout that time Ryan and I drifted apart. We did not know how to be "just friends" because we had connected so deeply and knew everything about each other and it was hard to turn that off. Throughout my relationship when we did see each other the spark was still there but we ended up arguing because he wanted to be what we once were and out of respect to my then fiance I didn't trust myself to be close to Ryan again so I wouldn't allow it. Ryan and I did not speak throughout the year of my marriage. He was not invited to my wedding which he now likes to say he would have objected to (I think he's kidding!). A couple of months after my marriage ended Ryan contacted me. He had no idea that I was out of my relationship. He simply was thinking of me and reached out hoping to reconnect. We became extremely close again and he helped me cope. I am now moving on from my marriage ending and Ryan and I are closer then ever. We still have that same connection we always had, still tell each other everything. All of our mutual friends have always said we had undeniable chemistry and they always thought we'd be together. If you saw us together you would think we were in a relationship. The problem is this, the timing never seems to be right with he and I. At the moment I don't want a relationship because I need to focus on me since my marriage has ended and I don’t think Ryan's ready either. So I am not looking for us to be together now but I am afraid to let yet another opportunity pass us by. However I am also afraid that if we ever did try to make something official I could end up hurt if he doesn’t remain faithful and it’d hurt more from him then anyone else because of how much we’ve had between us. I am going out and having fun with other friends and meeting new guys so I don’t feel like I am falling into a routine or limiting myself to him but it’s different with him. It always has been. We talk everyday, we spend a lot of time together, we cuddle, etc. so although now neither of us seem to be looking for a relationship I can imagine it may end up that at least one of us wants something again. My questions… How do you bring up feelings to someone you can talk about anything with but the one thing you probably need to? Since I don’t know what my feelings are should I just wait and see what develops then decide if we need to talk about it? Sorry this is long! I even cut some but there's just so much to our past and it’s so important I am afraid of missing out and/or messing it up, whichever way it goes!
– Tempting Fate (Again!), Worcester
TFA, I don't want to belittle your situation, but I am reminded of "90210." You are the Kelly. Ryan is the Dylan. That's right, folks -- I mean old-school "90210." I don't watch the new "90210" ... those youngsters with their skinny legs and fashionable purses. I was raised in the Andrea Zuckerman era. Long live Andrea Zuckerman. But I digress. Part of me thinks that Ryan's bad behavior stems from his first heartbreak with you. Part of me thinks he's just young -- and so are you. What seems to be missing here is an honest conversation. I don't understand why you cuddle, flirt, get passive-aggressive, love each other, date other people, and then get confused when all you have to do is ask for the answers. You talk to each other about everything -- except what's most important. You're either using each other as placeholders for real relationships -- or you're both too scared to admit you want to give the romance a real go. Regardless, the status quo is preventing you from real emotional intimacy. If this were "90210," it would go on like this forever -- and it would be mildly entertaining. But "90210" is no way to live. Let's make this a grown-up relationship, shall we? Ask Ryan, "What exactly are we -- and what are we avoiding?" Hopefully, he'll look deep into your eyes with a Luke Perry face and tell you the truth. Readers? What's up with Kelly and Dylan ... I mean, TFA and Ryan? What exactly do they want? What should TFA do? Share here.