On the cusp of a kinda sorta first date this afternoon. Although I’ve considered the repercussions, good and bad, about taking these tentative steps towards a potential relationship, I’m afraid I don’t have any great insights on just what I might be getting myself into. Does anyone ever though?

Here’s what I do know. I’ve been acquainted with Jessa for two years now. I made some effort back when we first met to make her my girlfriend, to no avail. I realized later that it was my own cowardice in putting myself at risk by pursuing a potential loving romance that doomed any chance of success. I felt like I was better off safe than sorry and I’ve pretty much been sorry ever since.

The past several days I’ve been chatting online at length with Jessa. I really appreciate the fact that she can carry her end of the conversation better than most. She is perceptive and offers some significant insights. She can also be brutally honest, but I kinda like that too. She has a great sense of humor and also seems to get mine which is always nice. I can tell already that she will not hesitate to challenge and push me as she deems necessary. Time will tell how she reacts when I push back. She is, however, open-minded and appears to have a healthy appreciation for the physical aspects of a relationship. At least she verbalizes them, time will tell if she is willing to demonstrate them in person.

On the downside, Jessa is exactly half my age. That’s really not a big deal in this culture, but it can be a bit disconcerting and somewhat intimidating. She has a 6-year-old daughter I’ve yet to meet but Jessa seems impressed by my experience as a single father (back when I was her age. Yikes!). I’m not sure at this point what else we may have in common, but I do know that Jessa is not into the hiking aspects of my life. I admit that it is a bit disappointing because I’ve fantasized about having someone to share my walking and Hashing experiences.

So, going into today’s date I’m keeping my expectations in check. I’m looking at it as having some pleasant company for the afternoon so I doubt I’ll be disappointed. I’ve got a batch of chili in the crockpot and I’ll bake up some brownies for dessert. Like many Filipinas, Jessa enjoys watching Korean dramas so I’m going to share one of my old-time favorites, My Sassy Girl, with her. After that, who knows? I’ve got plenty of beer. Or maybe a nap.

Here are some photos from yesterday’s walk that Scott took:

And that’s where things ended. Now to get ready for what may (or may not) be a new beginning.

Stay tuned!

UPDATE: It seems I used the “here we go again” post title way back in 2009. That’s from those days when I use to write about meaningful stuff like politics. What impressed me the most though was the robust and heartfelt discussion in the comments. Well, I’m still getting great feedback from the few that still come by to read my diary. Thanks for that!