Despite many circumstances I would not have imagined I would be okay with in a potential romantic relationship, I want to move forward with one that has what some might call a lot of “red flags.” For example, the man in question is in his mid-thirties, I’m 61; he’s a coworker; he’s currently in a long-term (4+ years) relationship with someone he has never mentioned to me, but I’ve heard about from others; and he lives three hours away by plane. Since having been in Scholars for going on three years, I experience circumstances as neutral, so when I examine these “red flags” what I come up with is there are objectively no such thing. For background, when I have done thought downloads and models about whether I want to be in a romantic relationship at all over the past couple of years, I haven’t wanted one because I don’t want to live with anyone, I don’t want to compromise on what I want to do in my life, I am not attracted to many people, and other reasons, but I am willing to make an exception for this one. Over the last year, as this relationship began to take on an emotional dimensions, I have had plenty of “should” or “should not” thoughts, but when I examined them in models they haven’t felt like they were coming from my authentic self. The model that I have settled on and like best is: C: This guy has expressed romantic interest; T: I want to explore a romantic relationship with him: F: Attracted; A: Engage in texts all day for over a year; allow him to plan regular trips to visit me; allow flirtatious comments from him and return them; fantasize about the relationship. R: An undefined romantic relationship. After lots of TDLs and models and multiple 20-minute coaching sessions, I am fine entering the relationship without knowing the outcome of this relationship, because do we really ever know? No. I currently believe I could handle the feelings that arise as a result, no matter what happens. I know we get to choose our delusions and this is the one I’m currently choosing and I just need to like my reasons. My thought is that I have made plenty of unconventional choices in the past, but not with relationships and I have to admit this seems a bit out there even for me. My question is: is there something that I’m missing or should be asking myself? Does this add up from an outside perspective?