Casual Dating and Cross-Country Moves

A year ago, I moved back to my hometown and reconnected with some old friends. I started hanging out with and then briefly dated someone whom I had known vaguely before but since moving back have gotten to know well. The dating was very casual and mutually enjoyable (but more intense for him emotionally) and stopped abruptly after we had sex. 

I understand that sex can be very intense and emotional for some people and that it is not necessarily the best thing to be doing when one person is more emotionally involved, so I understood his position. Ironically, I was seemingly the one more bummed out about us not dating but kept it to myself. 

He's never left our hometown, but he decided to move across the country to a state where weed is legal and a few of his friends already live, and he's completely normal not to want to be in any kind of relationship while he's planning to move away. I was fine, albeit totally, quietly bummed, going back to being friends, because I totally understand the need to break out and see new places. That's why I left our town in the first place. 

So, we stopped hanging out alone and only hung out in groups, until the other night when we spent the entire night outside a party talking and then walked home together. Then, the next day he came out with my friends and me and casually announced that he wouldn't be able to move as soon as he thought. (He figured he'd be leaving in a month or so.) I don't know if that is an issue of saving money/finding a new place to live/general malfunctions that happen when you move across the country or the fact that we hung out and flirted the night before.

I'm inclined to believe that he's just hit a budget snafu, and that's why he isn't leaving, but he is constantly updating us on how much money he's saved up for the move and stuff like that, so if it was, it would make sense for him to mention it, which he hasn't. He's also been incredibly lonely, lately, so perhaps our flirtation was welcomed and just threw him off his path momentarily. Or maybe it's something totally unrelated that no one has any idea about? I know it sounds self-centered to think that he may not be leaving just yet because of me, so to speak, but this is a man who gets nearly obsessed with women that he likes and has a very emotional and addictive personality (like several-stints-in-rehab-addictive). While I never hinted at the level of interest that he did, I was very much into this guy, and it really bummed me out and confused me (at first) when we stopped hanging out. 

I feel like every time we see each other things are drifting slowly back to the way things were between us (only a few months ago), and, while that is enticing, I just became comfortable with us building a friendship and with being happy for him to move and start a new chapter in his life. Should I step back from my own mentally solid feelings about our friendship and try to be open to him romantically/sexually? Should I say, sorry, but the chance has passed? Should I encourage him to keep going with his move? (Ill-advised by everyone we know, as this guy won't have a job or place to live besides a friend's couch once he moves.) Or maybe I should just keep my mouth shut, not respond to his flirtation and let him do his thing? Maybe there's even a better way of dealing with this that you, Rhonda, could please inform me of?

Friendly Enough?

Part I—Where I Try to Dissuade You From Liking This Guy

Oh, there’s a better way of dealing with this, all right. It’s for you to find a guy who doesn’t fixate on women or chemicals, who is doing more than just wafting through life changing direction by bumping into things and whose most thought-out plan exceeds, “I can crash on Dave’s couch when I get there.”

It’s important for you to get clarity from yourself before you involve this guy. You’ve been kind of knocking around, making decisions about the relationship only in response and reaction to what he says or does. First, determine by yourself if you’re really interested in dating him. Do you want to date him seriously? Would you be happy dating him until he moves? What if you start dating him again and he never moves? Do you want to date someone who’s planning to move somewhere with no job and no place to live and whose plan can be derailed by a night of flirting? Can you tell from my tone that my answer to all these questions wouldn’t just be “no,” it would be “hell no?”

Let me do my favorite thing and recommend a book for you. In The Defining Decade, author Meg Jay talks about the importance of making intentional decisions in your 20s in order to be on a good trajectory in the next decades of your life. I don’t know how old you are, but this seems to apply to you. You made a deliberate decision to move away and see other places. You’re making your adult life in the town where you grew up. Is this guy part of the adult life you want? Or is he the guy who’s in front of you right now? You don’t have to date the perfect person right now, but it makes sense to look for someone who’s at least in the ballpark.

Part II—Where I Pretend You’ve Heeded My Advice

So, you do a little soul-searching and decide that I’m right. He was a nice enough guy, and you had some fun together, but he doesn’t have his life together, and you’re building yours, so you’re really at different points, and he’s not really for you. Now, dial down the flirting a little. He doesn’t seem to have much direction, and he is easily knocked off course. He deserves to be making decisions, even bad ones, based on accurate information.

Part III—Where I Acknowledge That Everybody Does What They Want, Anyway

But, I’m as square as they come, and I know all the things mentioned above might not be deal-breakers for you. (Although I don’t know why the heck not.) If you do decide you want to date this guy again, as you kind of seem to, be clear about it. You’re not doing either of you any favors by sliding back into your old relationship without any clarity about whether it is a relationship and whether he’s still planning to leave. If you do want to date him, ask him why he’s not going to be able to move as soon as he thought. That’s your starting point. From there, you can go into, “Well, since you’re going to be around longer, would you want to try dating again?” Try to get some clarification about whether he still plans to move and what he might want and expect from the relationship. Be honest and forthright and clear about what you want from the relationship.

If his moving plans were indeed swayed by a flirtation at home, they don’t sound very concrete. The fact that there’s no job or housing at the other end of the move suggests the same thing. It sounds like he’s kind of letting things happen to him; be careful not to let that seep into your life. If he stays in town, you’ve lost the natural end to the relationship that the move would have provided. Is he someone you want to be with indefinitely?

I think those are the things you need to think about and work through. Now you just need to do the heavy lifting.