Dating Days; Part 4

These past four weeks have been exciting and depressing, but most of all they have been very informative and educational. As I mentioned a few weeks back I managed to get myself into what some might call a dating situation, but what I like to call a relationship. Granted, it hasn’t been the most conventional of relationships but then again, I’m not the most conventional of daters.

So in my last post I mentioned that the apple of my eye (although I wouldn’t tell her that) Estelle and I were scheduled for a follow-up date. This would hopefully make up for the travesty that was the first bowling/dinner event we engaged in. As previously noted, the plan for this new date was to take in some dinner and a movie. Of course, if my past dating life is any indication of future doings, things were not going to go as smoothly as I would have hoped. And alas, they didn’t.

Wednesday rolled around and I called Estelle to make arrangements for our Thursday dinner and movie “date.” I’d been hearing all about this new flick called the Hunger Games that is supposed to be just about the bees knees so I thought that would be a hip and cool talkie to take in post dinner. I saw in the paper that they were having a special showing on Thursday so I thought I would impress my lady-friend by taking her to the first showing of a hot new Hollywood movie. This would all be preceded by a nice (but not too nice) dinner at a nearby sports bar type place. That way, the random sports could provide some bits of distraction during dinner if the conversation was lagging.

I hope you’re sitting down because what I’m about to tell you seems so fantastic that it could only be made up, yet it’s sadly true. In my focused attempt to make up for the disgrace that was our first “date” I neglected to realize that the entire country is hip-deep in March Madness and a sports bar on game night might be a little raucous. And by a little I mean full on crazytown.

Four college basketball games; all at the same time; and lots of drunk sports fans didn’t make for the most inviting atmosphere for a date. We did spend lots of time making fun of the rabid sports fans but it wasn’t an ideal scenario. More importantly though, dinner took about an hour and a half longer than expected so the movie was definitely out as an option. That turned out to be okay because what I thought was a Thursday opening was really a midnight showing therefore it was technically Friday and I didn’t think Estelle would want to be out until two in the morning at a movie.

While things could have gone better, they weren’t terrible, and that is a plus in my book. If I’ve learned anything from this experience it’s this; check the times on your movies and make sure there are no sporting events when you plan a date at a sports bar. I realize they seem obvious, but when you’re only focused on the date itself, it’s easy to let some of the specifics fall by the wayside. I plan to give Estelle a call later on this week and maybe we’ll get this movie thing in for real. My feeling is that I’m finally wearing her down to the point where she thinks I might just be clever enough to spend some quality time with. Yeah, I’m that guy.

Dating Days; Part 3

In the ongoing saga of my dating prowess and the current person of interest in my life, things have taken a turn I didn’t expect. As I previously mentioned I was in the process of wooing one Estelle and setting up a second date. Unfortunately I was having difficulty getting in contact with Estelle. One of my astute readers mentioned last week that I should send several more text messages to try and coax Estelle into another outing with me. Since said commenter was a woman I thought her advice had to be solid and I went with it.

Well, four consecutive text messages later I finally got a response from Estelle. Of course, it was not what I expected. First, I was met with some unfriendly words about how I needed to stop bothering her. Then, after some charming explanation by me I was able to convince Estelle to give me a second chance and a second date. I decided I would play it cool and take her for dinner and movie. That way, if the dinner conversation was lacking, we could at least have the time during the movie where we wouldn’t have to worry about coming up with things to talk about.

Unfortunately our schedules have precluded us from conducting said date until next week. We’re going out next Thursday so that means I should either have really great news to tell you next weekend or a few depressing paragraphs about what went wrong. Either way, I think I managed to get back in Estelle’s good graces. I guess a little persistence does pay off.

Dating Days; Part 2

So as I mentioned in my last post, I went out on an interesting date with one Estelle. Things didn’t really go as planned since I forgot my wallet and then decided to make up for it by leaving a check at her house. Well, as I’ve recently learned that may have been a mistake.

Earlier this week I called Estelle to see if she had received my check to which she replied that she had. I was happy about that and asked her if it would be okay if she didn’t cash it until next week, since I was a little tight until my next paycheck. I couldn’t really tell if she was put off by that request because her response was difficult to gauge (being on the phone and all). Of course things seemed a bit more obvious when I asked her out for a second date.

After a brief and uncomfortable pause, I heard the stutter of a person that didn’t really know how to respond to a simple yes or no question. This could only mean one thing; Estelle was looking for an easy way to let me down. At first I was a little bummed out but then I decided it was her loss and I got right back on the proverbial horse. I went back to the grocery store to find another potential date (and to buy groceries of course).

As if lightening were striking twice, I walked down the frozen foods isle and once again spied another possible date for me. This time, however, I decided to keep on walking. Instead, I went home and called Estelle again to see if she really was sure that she didn’t want to go out again. I left her a voicemail and then followed it up with a text message just to cover all my bases. I have a good feeling that she’s going to call me back.

Dating Days; Part 1

So this weekend I did something I haven’t done in a long time. I went on a date. So I should start out by saying that I hadn’t been on a date in a long time prior to this but since I’m a man about town I figured I would give it a go. After all, how bad could it be?

I should probably start by telling you how I met the recipient of my date. So there I was, in the grocery store, going about my business of buying food. I was walking down the frozen foods isle and noticed a rather attractive woman seemingly lost among the freezer cases. By the look on her face I could tell she was unable to find what she wanted. As I approached her I noticed she was not wearing any rings (which is a very important thing to look for) so I thought it would be okay to try out a line from a movie that Steve Martin made famous.

I approached this stately maiden and said, “Excuse me but I don’t think you should be in here.” She looked at me and in a slightly surprised tone said, “Oh really?” “And why is that?” This was exactly the set-up I was hoping for so I could then follow up my original statement by saying, “Because you’re going to melt all this stuff.” Now at this point there was one of two ways this could have continued. She could have been completely disgusted and ignored me, or she could have given me a cute little laugh which would allow me to continue my charming ways. In this case she chose the latter (I’m such a pimp).

So after a few minutes of small talk, getting her phone number, and finding out her name; Estelle and I had a date this weekend. I think things went pretty well but I’m not sure how she felt. I played the chivalrous guy and brought her chocolates and flowers when I picked her up. From there we went to the bowling alley which also serves food so I felt good for mixing dinner and entertainment together in one place. Of course I forgot my wallet so Estelle ended up paying for everything. I felt bad about that so I went back to her house the next day and dropped off a check to pay her back for everything. She wasn’t home so I slid it under her door. I think I’ll call her later this week to see if she wants to go out again sometime.