Round 2, Date 2

JM- Match candidate #2

Chemistry from the get-go. Our emails were so full of witty banter I could hardly wait to meet him.

Date #1/2:

Our first date was on a Friday (as in just over a week ago) at a local bar. We met about 8:45. Immediately, I found him attractive and noticed that our witty banter seamlessly continued in person. Two drinks in, however, he reminded me that he had plans at 10 that he had committed to but that he really wanted to see me more tonight. So, he asked... would I be willing to wait for him at this bar for 20 minutes or so while he went and "made an apperance" at this birthday party? His tab was open, I could get whatever I wanted, I was social enough to make new friends while he was gone... blah, blah, blah. So, still being super-impressed with him at this point, I agreed to be the lady in waiting.

Alone at a bar on a Friday night while my date (1st date) went somewhere else. Awesome. I thought maybe he would invite me along, but I didn't want to ask... considering we had just met. But he preempted the issue, saying he would bring me along but it was a birthday party for a 25-year-old bitchy girl and all her friends who live in his building (he's forty) and they would give me the third-degree, asking me how we know each other, if we're together, etc. And he didn't want to put me through that. Likely story? Or possibly some prior history with one of the girls who'd be there? Honestly, at this point I don't know. But I do know he's very good looking, looks much younger than his age, and appears to have money. Hmm. So he bought me a beer and left.

Then, as expected, I made friends with the friendly folks at the table next to me and they bought me a shot. I think I then ordered another beer on his tab. Next thing I knew (and I'm pretty sure it had been just about 20 minutes as promised), he reappeared. We had another round and, all of the wonderful sudden, his hand touched the small of my back. At that point, I got so distracted I could barely formulate a coherent sentence. Then, we shared our first kiss. Just a peck, but enough to show mutual interest nonetheless. At this point, I was smitten. Granted, he had left me. But he came back. He hadn't planned on it, but he said he just wanted to keep hanging out because things were going so well. Swoon, swoon... hot, no children, successful, funny. And although he is divorced, his divorce was eight years ago and I felt that enough time had passed that he could be ready for something real. I even asked him what he was looking to get out of this whole match.com experience. He said all the right things... that, if he meets the right person, he is ready for a relationship.

So then we went to bar #2. At this point, he tried to convince me that this was now date #2 as: 1) there had been a change of venue, 2) we had had an an intermission when he went to his other obligation, and 3) he had entrusted me with his credit card. At this point, a little tipsy and loving the feeling of being loved on, I agreed. Although we had only one more drink, we suddenly became that obnoxious couple making out in the corner. I hate those couples. Whether or not I'm in a relationship. Seriously. He then walked me to my car, where we continued to make out. It was awesome... and I left with butterflies. Potential, I thought to myself.

Date #2/3:

We met at his place. A little too soon, don't you think? Look, I understand you have money and are clearly proud of your condo (so much that you are the president of the homeowner's association)... but I met you four days ago on match.com. So, after a "tour" of the very nice condo, we walked to the restaurant next door. We had a few beers, some appetizers, and two entrees. I did like the fact that I didn't have to worry about whether he would have enough money to pay for our dinner (as you probably know by now, my ex-boyfriend was a gorgeous yet unemployed musician/ artist). But I also can't help but wonder if these purchases are somehow like purchasing me. I will admit though, it felt nice to feel "taken care of." We did go back up to his condo (which was conveniently located next door to the restaurant) and there was some hooking-up. Nothing major. But enough for me to wonder... are we moving too fast? Does he really want to get to know me or does he have an agenda?

Date #3/4:

Last Friday. Exactly one week after we met. I was really worried he was planning on us going all the way on this date, so rather than have an awkward in-bed convo with him about this at what I'm sure would be an inopportune moment, I decided to just talk to him about it the day before, on Thursday. I told him I didn't want to rush things, as I could potentially actually like him. He said he understood and he was glad we were having this conversation. He went to explain how he's just a "very sexual person" and that clicking with someone you are dating in that department is very important. I agreed, then promptly reminded him that I had not even known him a week at this point. So we agreed on some boundaries for the following evening and that was that. I was actually pretty impressed with the way he handled it.

So I go over to his condo for dinner (yet again, he conveniently picked his place as the meeting point). He has a gorgeous spread of appetizers, champagne, wine, and plenty of beer. He is clearly trying to seduce me, I think to myself. But I play along. "How was your day?" I ask as I nibble on a yummy shrimp. He explains, and awkwardly returns the question. I actually go into a little more detail, as I had had a particularly rough day at work and just needed to vent. But somehow, I got the feeling that he didn't really care so much about what I was saying. That he just wanted to make out with me, fondle me, and see what else might happen if he continued to keep my champagne glass full. I even asked question after question about his family, his siblings, etc. I was genuinely trying to get to know him. He answered, but again, the answers felt more like a formality. Nor did he return any of the questions about my family. Red flag.

More later. Must break for now. Actually no, can't quit. He makes me lobster stir-fry (impressive). We ate at the table and afterwards began cuddling on the sofa. Then he says something extraordinarily cheesy like "you ready to move on to the bedroom?" In my drunkenness and knowing I had packed an overnight bag, I comply.

We hook up more. Again, not all the way. But more than the last date. Here's the kicker though, kids: After staying up until 2am or so and not getting much sleep (wink, wink), he wakes me at 5 something in the morning to tell me he always runs 18 miles on Saturday mornings... so I'd need to get ready to go. Whiskey. Tango. Foxtrot. Don't you think this would have been useful information to mention when you invited me over for a Friday night overnight date and filled me with considerable amounts of alcohol? So we get up, he makes me coffee (even puts mine in a to-go cup... so considerate!), and by 6:15 or so we're out the door and I'm being driven to my car.

So what to make of all of this? Well, for starters, should he get another date (which is up in the air at this point), I told him that I leave for work at 6:45am Monday through Friday. Hence, Saturdays and Sundays are my days to sleep in. I asked him if he ran so early on Sunday mornings. When he told me that he did not, I told him that if we ever did this again he needed to invite me over on a Saturday night.

I felt like such a fool. Don't you think that mentioning to your overnight date that a 6am departure is part of the deal is kind of key? Especially when we're drinking late into the night and not getting much sleep due to our hooking-up? Thought that lack of disclosure was pretty much his biggest jackass move yet. And to add fuel to my fool fire, I had brought a change of clothes because I has assumed we were going to sleep in and then maybe go to breakfast. Wow, did I feel like a winner.

So that was yesterday and I haven't heard from him since. And tomorrow is Valentine's Day. Perfect timing. As if I didn't hate the "holiday" enough when I'm single, not I'm in this weird in-between phase. I doubt he'll call or do anything. I'm over it anyway. Back out into the dating jungle, I'm supposing... wish me luck.