Here’s the thing about me and dating – I consider myself to be fairly awkward. I feel like I’m constantly tripping over things, whether my own feet or my tongue. I also try to do things “right” or the “normal” way — even though I fully realize those are constructs and there is no such thing as “right” or “normal.” 

My therapist pointed out that part of it might be that I can’t turn my academic brain or analyst off. I’ve read a lot about dating and marriage. Hell, the manuscript I’m currently working on it about emerging adulthood and marriage. It complicates things! A major portion of one of my classes focuses on dating norms in today’s society. That also complicates things! 

Add into this mix my habit of overthinking and you get a lot of wondering if I should do or say things and what they might mean and what he might think… it can get exhausting. 

And he picks up on it, too, pointing out that I may or may not worry too much. 

Right now, my dilemma is that he claims that he is weird with women. And he’s reserved/cautious. And he’s uncertain that he wants a relationship. We’ve agreed to do baby steps. 

He does want to spend more time with me. 
Sooo… you have me. And I like things such as plans because they help me not spin out of control with my overthinking and questioning. I’m not a big fan of “games” or “playing hard to get.” I am horrible at pretending like I don’t care because I do care. 

Here’s how our date set-ups have gone:

At the beginning of September, he suggests we meet. Says his first available weekend is the end of September. I suggest meeting the next day instead at Oktoberfest. We meet the next day. 

End of September, I suggest we hang out. Other plans come up at the last minute for him. We move the date to the following weekend with a specific date and activity: Cedar Point. 

Last weekend, I was in Cleveland anyway. I suggest we hang out. We do. It’s sort of quirky. We grade together then watch the Tribe game. 

I don’t want to keep setting up our get-togethers… and it would be nice if he came to my end of town, although it is harder to come up with things to do. 

It would just be nice if he was like, “Hey! I’d like to see you! Let’s go do this if you don’t have plans.” I just don’t know that he takes me into consideration like that (yet). Or, given his self-professed weirdness with women, that he will. 

I think I will ask him if he has plans this weekend, then inform him that it’s up to him to set our next date. That way it’s very clear and I don’t get frustrated by waiting for him to do something without the possibility of him not realizing he needs to do it.