I Think I've Got A Date!

Yes, believe it or not, it's true. I  may have my first honest-to-goodness date with a woman on Monday night! :-) I'm pretty excited at the prospect. I am not trying to get myself too excited about things, but it's a pretty huge move for me.

In a previous post, I described how I first met Laura. And then, later on, I worked my way into arranging a "coffee date" with Laura and I described that in this post. Well, it's been slow going since then, but it has been going. Let me fill in some of the gaps.

Right about the time of our first date, Laura had just accepted a job offer as an IT manager with a smaller company in the area. As I mentioned in the post, she wasn't feeling all that well, but we did have a good conversation. It started off with talking about the stuff that was the actual reason that I suggested that we meet, then I moved on to what she was doing and some more personal stuff about the two of us.

It was at that point, when it became clear that she was going to need to leave early and it wouldn't go on beyond coffee that night. I was hoping that it would turn into dinner, as I was hungry anyway, but it didn't. Still, we'd had a good time and I felt that there was a sufficient base for further conversation. When I got home, I sent her an e-mail thanking her for coming out and suggesting that we set up another time when she was feeling better and had more time. At this point, I was already being more bold than I have probably ever been in my life! Feeling good about it, I was.

Over the next few weeks, we traded voice mail and email. By the time Thanksgiving rolled around, we had established that she was going to travel home to visit with her family. I told her that we should touch base after she had returned and gotten situated a bit in her new job. The holiday came and went. I sent her a note early the week of 08 December. So up until now, it was all playful banter back and forth and pretty non-committal about a next "meeting" (or date, as I was thinking)... everything was still in "professional mode".

That Friday night, as I was heading to an appointment, I finally got a phone call from her. I was likely going to be late because of it, but I wasn't going to miss my chance. We talked a bit about how the new job was going and chit chatted a bit. It seemed like we were getting close to the end of our call and I found myself faced with a choice:

Step up and take my shot at asking her out on a proper date OR let it go

I had already established that I was interested in her and I asked myself a key question -- what's the worst thing that could happen? Well, of course, the answer is -- she could say "No, I'm not interested". Rather than think of that in one of the myriad of ways which I could use to further lower my limited self-esteem, I decided that the thing to do would be to just use it as an opportunity to practice. After all, if you don't take a chance, you'll never really know. Every opportunity you pass on is one that is guaranteed not to turn out.

I got my nerve up and came right out with it... something to the equivalent of "you know what, I think that you and I should go out for dinner. I think we'd have a really good time together". I know that she wasn't expecting this and it kind of took her off guard. Why? Because there was a bit of a delay on the other end of the phone. The proverbial "pregnant pause". Well, she came back and said "OK, that sounds good".

We talked a little bit more about the logistics of how it might work. We discussed that the holiday was coming up and that she was again considering (but hadn't decided on) whether or not she was going to go home to visit her family. Just based on the evidence I'd already had, it seemed to me that family was very important for her, so I wasn't surprised at her answer. I told her that, if she decided not to leave for the holiday, we could target something over the break. Otherwise, we could look at doing something after the first of the year.

Well, as it stands, she did go home over the holidays. I sent her a grand total of two e-mail messages over the holiday break to keep myself in her awareness, but not be overly pushy. The first drew a tepid response "apologizing for not getting back sooner. Keep in touch and let me know when was a good time to chat". Hey, not great, but not terrible. After the start of the year, rather than send another e-mail (which always had a bit of a delay in responding), I decided to place a call. After this, we traded VM a few times, still on the tepid side.

Yesterday, I said to myself that "it's time to take some bold and decisive action here!". I called her at the end of her work day and told her (something like):

"I know that you've been working really hard and a lot of hours. Given that, I think you need to have some time off to have some fun. Working too much is just not good. So I am going to propose that we go out and have either lunch or dinner either Saturday or Sunday. Just let me know what works for you and we'll do that. Look forward to hearing from you soon"

I thought to myself -- very shrewd move! You extend the invite and now have an opportunity to follow up. I wasn't sure whether or not she'd actually get it on Friday night and I really didn't care, I was going to follow up with her on Saturday anyway. This morning, I had the objective of contacting her squarely in my sights. I thought about it and started to call -- then I stopped. I said to myself "hold on a minute... I haven't actually gotten her by phone yet. Why don't I try texting her?"

So I did. Here's how it played out:

Me: Hi there! Me here. Thought I'd try you via text. :-)
Me: Wondering if you've listened to the VM I left yet?
Her: Yep unfortunately heading to work here in a bit

OK. So, strike one. I am undeterred and will keep going.

Me: OK. Sorry to hear that. What about tomorrow?
Me: Thinking a nice, casual dinner somewhere...
Her: Have dinner with the fam tonight, sorry

OK. Good. She missed the part about tomorrow, gives me another shot. So, let me reinforce her choice to be with the family and go to talk about tomorrow...

Me: OK. Got it. Think that's a good thing.
Me: Would tomorrow be an option? Your call on time and location...

OK. So, now, there's another "pregnant pause". A significant gap in hearing from her. I started writing a message to her that was along the lines of  "I'm not good at this... if you don't want to do this, it's ok..." blah, blah, blah. Before I could hit the send button, I get a text back from her.

Her: Perhaps monday but uncertain on your schedule
Me: I think Monday would work just fine
Me: I hope you have a good day at work and a good dinner tonight. Will connect as we get closer to firm things up. Thanks!
Her: Sounds good!

Fortunately, I gave her enough breathing room to reply before I stuck my foot all the way down my own throat!

At this point, nothing has been confirmed, but it's moved forward tangibly and significantly. I am now half a heartbeat away from actually having my first real date in over 20 years with someone that I am genuinely attracted to.

I am super excited about how all of this has gone. This is very, very good. I don't know quite where it's going, but these are steps in a good direction. The only objective is to have a good time and get to know someone.

I can do that as easily as breathing.