It's at Oberon in Harvard Square, and there will be drinks and books and dresses with pockets.
I wanted to know if anyone has ever successfully transitioned from a casual to serious relationship. Is it possible? Yes, I am the one who now has the feelings. After years of casually seeing this guy and trying to date other people, I've realized that he truly makes me happy and that I see a future with this man.
We have known each other for seven years. We dated, slept together many times (he's the best ever, FYI), and then moved to different cities. We always chatted via text, casually, and if we happened to be in the same place at the same time, wonderful. We would hook up. Then ... crickets. Sometimes it was months. And with the crickets, it was on both of us. I didn't actively reach out and he didn't either, but when one of us did, the conversation didn't stop. I will say he is not one to make plans or put anything on the calendar, which is why I think getting to the next level might be impossible.
I have a busy life, he does too, and now we live about 1,000 miles apart. I'm in my mid-30s and he's 40. Neither of us have been married or have children. My job will let me live wherever I want, so I have hinted about a move to his city. He has not taken the hint. Mainly, I want him to say, "It would be amazing for us to live in the same town and try this." He hasn't.
He knows how I feel. He tells me he cares greatly for me. I do know he is not married or living with anyone else (many of my friends thought he might have gotten married at one point and just kept talking to me). I think he's just a guy who likes to be alone and doesn't see marriage in his future. He has said that he's open to having kids, and if he did, he'd want to have them with me. This man is so confusing!
I have dated others during this time, and I am actively trying to date now, but no one compares. I should say: This "seeing each other whenever" thing worked for me for six years, but now I want more. Do I just take the leap and move? I would get my own place. I know you can't change a guy, but doesn't everyone want to settle down at some point?
"... doesn't everyone want to settle down at some point?"
No. Also, some people settle down alone.
"Do I just take the leap and move?"
No. That would be a huge risk, and you'd be taking it for someone who has no plans to be with you. "Surprise, I live here!" has been a really great storyline for a show on the CW, but it's not so simple in real life. Also, I get the sense that this isn't a place you'd move if he wasn't there. What happens if you uproot your world and he's not interested?
A better option is to plan a visit – and a real conversation. You say he knows how you feel, but ... does he understand how much you want this relationship to change? Have you asked him what he thinks would happen if you lived in the same city? If not, it's time. An in-person talk is ideal, but if that's impossible, make it happen by phone.
Remember that this man is great at swooping in for excellent sleepovers (and some romance), and then he's gone, leaving you wanting more. All you know is the excitement and the crickets. The rest of it is your imagination.
You need a lot more information before you start planning your life around this person. Instead of building the fantasy, get some real answers.