Obscurity Knocks

Earnest, empathetic, industrious, unpretentious, gay Virgo in Milwaukee with a great life, amazing friends, and a wonderful family.

Friday, July 06, 2007

Mid-year dating report

Now that 2007 is more than half over, I thought I'd post an update on my dating life. I've been on dates with four guys so far this year. At this stage, only one shows any inkling of promise.

1. Glenn. I met him on Yahoo Personals in January. He had a very interesting and eclectic history: currently working on a degree in counseling psychology, formerly played drums on a cruise ship band for a number of years. Based on personality, I was interested. Unfortunately, I felt no physical chemistry with him. I could not imagine kissing him, let alone anything more. Nothing against Glenn, but I just wasn't feeling it. Plus he lives with his parents at age 34 or 35, and that doesn't earn him any points. I certainly wish Glenn all the best.

2. Jay. I also met him on Yahoo Personals. Like Glenn, Jay had an interesting history, working for about five years in residence life positions in higher education, mostly in Southern California. Then he changed careers completely and was just finishing up a class in massage therapy. It would be a nice bonus to date a message therapist. We had a nice coffee date, but I don't think that either one of us felt much chemistry. I think it was mutual that we didn't want to pursue things beyond the coffee meeting. I'm of the opinion that you can't force chemistry when there's none there. I hope that Jay finds much success in his message therapist career.

3. Jason. I met Jason over a year ago through Friendster. We had a friend-of-a-friend connection owing to the fact that we both went to college at Marquette. We had our first date in May 2006. I'm known to be a tad high-strung, but Jason makes me seem like the picture of serenity. I was amused and smitten by his handsome looks and intense energy. We had two other dates in late spring/early summer 2006, but then he sent me an email saying that he was not in a place where he could handle a relationship. Fair enough, I thought, and better that I found out after three dates than after months of dating. At least he was honest about where he was in his life, and I appreciated that. Then in March of this year I came across Jason's profile on Match.com. Based on his profile, it appeared as if he was looking for a serious relationship this time. So I sent him an email saying hello and asking if he wanted to get together for lunch sometime. We met for brunch about a week later, and it was our best conversation to date. I was pleasantly surprised that he remembered so much about me after almost a year. He recalled specific details about my job, family, and favorites. He had also made much progress with his career, living situation, and workout schedule since we last spoke. Thinking like something might be happening, I went home from brunch feeling rather happy. Soon after I arrived home, Jason called me to ask if I wanted to go for a walk. We subsequently took a two hour walk on a warm sunny spring day in Milwaukee. Again, I thought that this gesture on his part showed real promise for the future. Next we agreed to meet for dinner. We had another pleasant conversation over dinner at Cafe Hollander. So much so that on the way home, I tried to kiss him. He said that he wasn't ready for that yet. I was slightly dumbfounded given what I perceived to be his intense interest in me, but I found solace in his use of the word "yet." Jason then contacted me not too many days later asking if I wanted to grab dinner that evening. I already had plans, so I suggested meeting one night later that week. We agreed to do just that, with a scheduled date at the Cheesecake Factory at Bayshore since that was on his way home from work. We both showed up at the appointed hour, but Jason forgot to tell me one important thing: he brought a friend along. This friend was also a gay guy. Assessing the situation, I figured I had three options: (1) grin and bear it through the dinner and be as civil as possible, (2) make up an excuse about why I needed to leave the restaurant immediately, or (3) ask Jason what the f*ck this was all about. As my good friends would willingly tell you, the Steve of old would have picked option number three. However, I'm trying to be more mature and wise. So I selected option number one and figured I'd try to figure all of this out. Obviously Jason was trying to send me a message, one that was received loud and clear: he wasn't interested in dating me. After an excruciatingly long dinner, I wasn't 100 percent sure what the deal was with the friend. At first I suspected that Jason was dating this other guy, but neither one of them gave any indication that they were a couple. Then I wondered if Jason was trying to set me up with his friend. That could have been the case. The friend was definitely a nice guy, but he wasn't flirting at all with me, and I wasn't interested in him in a romantic sense. Mostly because the friend is closeted, and I don't have much patience for guys who are closeted as I inch toward my mid 30s. So I endured the dinner, listened to Jason talk about some hot guy at his gym, and did a slow burn. But I kept it together, was civil, even nice, and said my goodbyes after dinner. I haven't contacted Jason since that whole episode, although I'd love to tell him off. Again, the Steve of old would have felt compelled to communicate in a scathing way with Jason, but I figure what's the use? He obviously isn't interested in me, so I move on, with yet another flake to add to my dating history.

4. Jerry. I'm embarrassed to admit this: I met Jerry on Manhunt. Yes, the lowest and dirtiest gay site out there. Most of the guys on Manhunt aren't looking to date, let alone find a boyfriend; they're seeking instant gratification, which seems to be the theme of 21st century living. In any event, we started chatting, the conversation was not sexual at all - thank goodness - and we agreed to meet for dinner in a few days. We had dinner at Harry's, a restaurant where I've had many fun meals over the years. It was without question the best first date I've been on in almost three years. I felt an immediate physical attraction to Jerry, who is handsome, cute, and has a great smile. He's an excellent conversationalist, but was also a bit nervous, which made him even more attractive in my eyes. We seemed to click throughout our conversation, so much so that when I asked if he wanted to get ice cream at Lixx after dinner, he readily agreed. So far the only problem was that Jerry lives in Chicago and I live in Milwaukee. But he just began a consulting assignment here in Milwaukee that will last for at least a year, meaning that he's here Monday-Thursday each week, then back in Chicago for a long weekend. Since the dating pool in Milwaukee is virtually nonexistent, I figure there are far worse things than dating a guy who lives in Chicago. On my way home I was cautiously optimistic. Then about ten minutes after I arrived home, my cell phone rang and it was Jerry calling to say, "I just wanted to let you know that I had a great time tonight." Needless to say, this call made me feel happy and excited about where this could lead. After that, we tried making plans, but I was headed out of town for eight days, he had to make a business trip to Britain, and he seems to lead a very active social life in Chicago. So we had no success in scheduling anything, a proposition further complicated by the fact that he's only here in Milwaukee Monday-Wednesday nights. A couple of weeks ago I decided to chalk this up to a nice guy, but too many obstacles such as the Milwaukee-Chicago distance and particularly his active social life - one that he's evidently not willing to make room for me. Then a few days ago he emailed me asking if I was free for dinner on Tuesday. The email said how much he enjoyed our prior dinner and said he was looking forward to seeing me again. After consultation with Ruben and Nate, I agreed to meet him on Tuesday. So we'll see what happens. My expectations are low, but you never know what might happen. I'm definitely open to the possibility of dating Jerry and letting him into my life.


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