A guy giving you his cell phone case is the 2015 version of the letterman jacket. I don’t know if that’s really true, but I like the sound of it. Sometimes it’s the littlest things that make me go, ok I dig that. After a few very difficult months following a breakup and having to put Maximus to sleep, I haven’t really cared about dating again. I will say I have at least been living. Going out and doing new things, going new places, and being open to meeting new people. Time is a weird thing. You can’t change it, you can’t get more of it, and you certainly can’t make it move faster when you’re having a hard time. But, sometimes, time has a way of being there for you when you’re ready.

I must say, I don’t know what it’s in the air lately, but I’ve been on fire. I don’t mean that strictly as dating goes, I just mean in general things have been on the up and up. Or should I say, the stars are aligning? Is that right? You get it. Between a really flawless trip to Cuba, some awesome things happening in the personal lives of those around me, it finally seems like things are turning around. Maybe it’s just because after I had to put Max to sleep, I felt a sense of lightness. As bad as that time was, I suddenly felt like things couldn’t get much worse. I lost two pretty important things in my life back to back, but I can’t change it and I have no choice but to move forward and start a new chapter in my life.

Now, I have learned that I am way too closed off when it comes to dating. I give literally NO ONE a chance. That’s my flaw and I’m working on it. I have just always said I’d rather be alone and wait for the right thing than settle for something less than. Easier said than done for sure, but I sense that is what is right for me at this point in my life. Going on that journey to Cuba with my best girlfriend and meeting two incredible new girlfriends really gave me some sort of glimpse into what I need in my life. A sense of clarity and comfortability I suppose. I have really needed to find a way to be proud of myself. I am not insecure so that’s something I have always had a hard time empathizing with others on. I think a flaw of mine has been feeling too average and not being proud of myself out of fear that would seem narcissistic or something. I was often trying to fix things in myself instead of focusing on what I am good at and what I do have to offer. The past few months has shown me a real different side of myself. I am strong and independent. I have a career and great friends and was able to go to Cuba on my own!

Though things aren’t perfect, I finally stopped and realized I have come a long way on my own and that is something to be proud of. Maybe I just got lost in wanting someone else to be proud of me and I lost my way for a bit. So going back to the little things I dig romantically, I finally opened myself up to someone I’ve known mildly for a few years. He has seemed mildly interested but has known my situation. I guess the timing just worked out because we hung out and I was really impressed. I wouldn’t normally talk about something new but honestly it’s more because of what I realized in the situation that made me so happy. Whether this works out or not isn’t even the point. It’s more that I found myself going, “okay Jenna you’re on the right track”. This guy seems to have an understanding of where I’m at and I feel so good about that. He has his shit together (as far as I can tell) at least when it comes to adult stuff. He has a pool. No, you misheard me I said he’s really cool:)

But really, to be able to chill at his house and talk about his older dog who isn’t well and have empathy both ways was really cool for me. It felt like there was no pressure either way and kind of let’s just maybe see where this goes kind of thing. Simple right? Maybe too simple to be true, but I had a moment where I was sitting outside drinking coffee with this person, playing with their dog and looking at this house they’ve made a home and I went, this is where I’m at. This is the kind of thing I am into and I feel like I have some sort of direction on the type of person I am going to date next. Maybe it’s not him, maybe it is, but the point remains so clear. Someone that owns their life this way. Has interests that aren’t “whatever my friend are doing tonight” type of guys that I meet. The kind of guys that does his own thing whether it’s alone or can be confident enough in himself to just lead the way. It’s not lost on me that this means I have to date someone older than me. He mentioned something about being at a place where he doesn’t want to do the grass is greener thing anymore. Obviously only age can bring that kind of clarity to a guy. But I’ll tell you what, I really like that mentality. I’m not that worried about this and for now I am just chill. Actually, I think I am always really chill when there’s a sense of genuine transparency. I just want to be able to still do my own thing and have someone who wants to share in the fun life stuff as well as the boring Sunday mornings that really aren’t boring at all when you’re making new memories. He has already learned not to make bets with me on soccer or True Detective. If nothing else comes from this, I’m at least getting a really great pool party out of it:)