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Previously in TMI: Once upon a time, I met a guy named Bill and I tried to date him. He was find spending time with me, but there was no affection at all. Guess I was stuck in the friend zone. (In essence: I dated a guy who wasn’t dating me.) No problem, I wasn’t in love with him and I was happy to be friends with him and help him with his computer on Monday. But before this Manic Monday, I had to get through the weekend of Market Days*.

(*Market Days is a street festival in Chicago that happens every August in the highly gay North Halsted neighborhood. It attracts drama from all around the country.)


In some alternate universe, I follow the 7 Habits of Highly Effective People. (Truth be told, I have many habits; none are highly effective).

Be that as it may, the second habit is "Begin With the End in Mind". So the end of the blog entry is:

"So I'm the jerk."

And away we go.

* * *

Saturday morning I awoke to a text message from Bill.

“Are you awake or are you hung over?”

Terrific. I have to deal with this first thing in the morning. “I’m awake. Are you sober?” I reply.

“Sober. What are you doing tonight?”

He knew it was Market Days and we had even talked about going together albeit a couple weeks ago. “I’m probably going to Market Days. You?”

“When time are you going?”

“Probably between 5 and 7 tonight. What about you?” (I decided to go later in the evening, that way all my frenemies would be good and drunk. I needed every advantage I could get this weekend.)

“Sometime tonight,” he responded.

“Sounds good. I’ll let you know when I’m heading out. We can meet there if you want.”

“Sure.”

So, let’s summarize: Bill reached out to me. He asked me about my plans for the day. He agreed to meet me at Market Days in the evening.

I left for Market Days at 6 PM and texted him that I would be there by 7 PM.

Crickets. No response.

At 7, I texted him that I was walking in to the fest. He texted to say he would shower and meet me there. Considering he lives three blocks away from the festival, I expected him between 7:30 and 8.

There was an $8 cover charge to get into the fest, which unfortunately didn’t include bottle service. Perhaps next year?

While I waited for Bill to get his act together, I meandered around the fest. A man with a unicycle ran into me. In his defense, he apologized twice. On the other hand? He brought his unicycle to a street fest. To say Market Days is crowded is an understatement.

And don’t get me started on the people who bring their babies, strollers, dogs, goats, bikes and wheelbarrows to the fest but then act indignant when you don’t immediately get out of their way as they try to walk through the sea of drunks.

I also walked by a booth where I saw a sign that read, “We’ll Pay You $1 a Minute to Watch Our Video!” Hmmm. I thought they might have been paying people to watch the new Jessie J video (which would make sense). Upon further inspection, I could see that it was run by the animal rights people and the video was probably not going to much fun.

No thanks. I’m good.

I walked the fest for 2 ½ hours and hadn’t heard a word from Bill. I figured he wasn’t coming out and I decided to leave. I could have texted or called him, but I decided that I wasn’t going to chase him. Remember, he asked me if I was going tonight. Sorta.

I decided to go hang out at Big Chicks. Of course, 10 minutes after I left Market Days, Bill texts me, “Hey, where are you?”

“I’m gone. What happened to you? I thought you were going to meet me out.”

“I’m sorry, I got a phone call. Where are you?”

Ugh. A phone call? Give me a break. But I told him where I was heading and invited him to meet me there.

Crickets.

An hour later, I texted him and asked if he was coming out.

Nah, he was at Market Days now.

So at this point, I may or may not have been drinking and texted him, “My fault. I misunderstood. Thought you wanted to hang out today. But you just wanted to go to Market Days.”

This prompts a phone call from him. I step out of the bar and decide to end this nonsense.

“How’s the bar?” he asks. “Got any numbers yet?”

What? Wait. So now we’re asking each other about how much action we’re getting? Okay, I can play that game.

“Three numbers so far.” (Spoiler Alert: I did not get any phone numbers.)

“Whu? Really?” That seemed to take the wind out of his sails. So I decided to push it a little further.

“And two blow jobs.” (Spoiler Alert: I did not get any blow jobs.)

“WHAT?!” I think I heard him do a spit take over the phone. “Are you alright?”

“I’m fine. I’m having a great time.”

“I guess so. Listen, I’m gonna come by right now. Don’t go anywhere.”

“You sure? I’m fine.”

“No, no. Don’t go anywhere.”

Stop me if you’ve heard this one, but… three hours later, no Bill.

It’s funny, because I didn’t let it spoil my night. I had a lot of fun dancing and drinking. (No numbers, no jobs.) But I was pissed that he didn’t show up. I’m not above getting my feelings hurt. I’m human.


Sunday afternoon, he texted me. Huh? No phone call? Nah. Here’s the message he sent:

“I’m so ‘sorry’ about last night. It was all my fault. Are we still on for tomorrow? 6 PM would work for me.”

So let me get this straight. He stood me up at least two times on Saturday night, and now he wants to know if I’m still coming over to fix his computer tomorrow? Ugh. I wasn’t ready to deal with him, so I ignored the message.

A couple hours later, he texts me again. “Let me know if you’re coming. I need to get to the store to buy food for dinner.”

Must. Not. Reply. In. Anger.

But by 8 PM, I was ready to deal with this. I figured that I should call him and just find out what happened. He could have a good reason for yesterday (I’m sure he doesn’t, but…)

I dialed his number, but no answer. I left a message simply stating, “Hey. It’s me. Just calling to see what happened to you last night. Call me back.”

Flash forward to Monday at noon where he texts me (he never returned my phone call): “I just want to know if you’re able to help me with my computer. I need to know ASAP.”

Ugh. No phone call? We’re going to do this with text messages? I cannot deal with this foolishness.

Until he calls me an hour later. “Hey, I texted you. I’m going into the market. Are you still planning on coming by?” He sounds a bit perturbed.

“Uh, yeah. About that. I’m not planning on coming by until we straighten out what happened on Saturday.”

“What? You’re still on that?”

“Yeap. What happened to you?”

“I don’t have time for this. Are you coming over or not?”

“Not today. I would like have a conversation about Saturday before we get together again.”

Now he just sounds angry. “I don’t have TIME for this now. I’m in between jobs.”

Cool as a cucumber (because I quit caring about 24 hours ago), I say, “That’s fine. Call me when you have time to talk.”

“Goodbye, Carl.”

Now, I could have taken him up on his offer to stop by his place and had that conversation in person. Would that have been better? Perhaps.

But I knew he only wanted me over there to get his computer fixed. Not once had he shown me that he was any more interested in me than my skills with technology. So I wasn’t really in the mood to put myself out. Childish? Perhaps.

Regardless, I thought he would call me after he calmed down we would get through this.

Whoops.

That wasn’t case. An hour later I received the following text:

“Huh. I thought you were more mature than this. You are using the fact I had asked for help to make me explain something so petty. I wanted you to see my place and cook for you to show how much I appreciated you. As for Saturday night, I just said that I wanted to go out and I would see you there. You weren’t there when I showed up and it was no big deal. I hadn’t slept well the night before so I went home. I didn’t pick up the phone last night because I was asleep. I’m disappointed how you responded to something so petty. I didn’t expect it from you, someone I thought was better than that. Just when I began to really like you, you showed this part of you. So disappointing. Thanks, but I don’t need your help. I thought you wanted to help me. Please, don’t respond.”

So, I’m the jerk.

Of course, when he asked me not to reply, he left me with no choice.

“Bob, I called you yesterday to talk about this. You had said that you don’t like having conversations like this with texting. I thought this should be done over the phone. But you didn’t return my call. No big deal. I figured we would just talk today. But if you want to do this with text, cool.

I was excited to see your place and you. And I’m happy to help you with your computer. I just want to enjoy my time with you, and not hold onto a misunderstanding. To me, it’s important that we clear things up before we get together.

As for Saturday: I spoke with you at 11 PM. You said you were on your way. I stayed at Big Chicks until 2 AM. The bar was pretty empty when I left. Not sure when you arrived. But even if you got there after 2 AM, does my time mean so little to you that I should be expected to wait 3 hours for you?

And this is after you had also agreed to meet up with me at Market Days (you texted me earlier Saturday morning). I texted you at 6, said I would be there at 7. I texted you when I got there. You told me later you would shower and meet me there. I didn’t hear from you until 9:30. The courtesy of a heads-up would have been respectful. I deserve that.

It all came down to the fact that I wanted to spend time with a friend. I understand something might have come up, but all you had to do was text me, “Sorry, I can’t make it” and I wouldn’t have waited for you.

You may think this is petty. I don’t think it’s the end of the world, but I feel it deserves a conversation. I would do that much for you. In fact, I would respect you enough that if something came up and I had to cancel, I would let you know why. I thought you cared enough about our friendship to not stand me up twice in one night. I thought I was more than just some guy at a bar.

I’m still open to that conversation. If you’re not, I respect that.”

Still haven’t heard from him.

So I'm the jerk.

I’m not going to say that say that it feels good to end my friendship with Bill but the logical part of me tells me that I probably dodged a bullet there. If he were to call me back and want to talk, that would be fine. But I’m sure he didn’t even read the message.

Such is life.


Next: Either “Kingpin” or “Four Dates and a Blow Off”

Previously in TMI: Heart was broken. Heart has mended. What doesn’t kill you, blah blah, blah. Ready to date.

I know that as I get back to dating, I have to put myself out there. I can’t sit at home. Sure, my heart is safe when I stay home, but I’m not meeting a lot of guys in my living room these days. It’s time for me to start being social and taking chances. But I’m the guy that’s had a 40-year marriage to a little something I like to call “control”. And I definitely wear the pants in that relationship. I’ve been trying to hide this from my therapist but he’s a smart cookie. I think he’s picked up on this because he challenged me to go out once a week. 

And I have to go to places where I can find other gay men. 

And I have to find one person to talk to. 

One person. 

Okay, you know how there are some people who are all, “I LOVE a challenge? LOVE IT!!!!” I’m not one of those people. I would so much rather there wasn’t a challenge. 

Unless, of course, it’s a challenge that I think I can easily meet. 

But this is not one of those challenges. Ugh. 

And yet, the guys haven’t quite been lining up at my door to meet me. Anyway, about a month ago, I decided to head out to Big Chicks (Yes, I HAVE discovered how to create hyperlinks. Thanks for noticing!) and make this happen. Funny thing happened when I got there. The bartenders slipped a bunch of alcohol into all my drinks and I found myself  letting my guard down a tiny bit. But I still found it hard to really introduce myself to anyone. Don’t get me wrong, the vodka helped me make googly eyes at a number of guys, but I wasn’t all, “Well, hello there, handsome. How’s your night going? Interested in a drink?” Nah, it just made me jump up on a box and dance to Kylie Minogue songs. 

P.S. Why is it every time they play “Get Outta My Way”, I feel the need to lip synch (for your life) and sing it to some nonexistent boyfriend who never dances with me? I have yet to find this person, but when I do find him, I know exactly what I’m going to say to him.

Or at least lip sync. 

Regardless, even with the added therapudical (that’s a word, right? I’m too hung over to spellcheck, so just work with me) support from my drinks, I decided this would have been so much easier on Grindr, yet somehow I doubt that Grindr counts as social interaction. But I digress... 

After much on-a-box dancing, I found myself at Jackhammer and my buzz was still hanging in there. Somehow I found the courage to go up to one guy and introduce myself. 

And his (fake) name was Bill. I found the biggest, toughest looking guy I could (way to set myself up for success there) and said hello. We talked for a few minutes and had some awkward conversation (the only kind you can have at 3 AM). Then said he was going to go outside and have a cigarette. (Remember this. It’ll be important down the road.)

I figured that was a polite way of brushing me off but I figured that I had at least talked with one person. Mission accomplished, right? 

Nah, that would be too easy. He returned about 20 minutes later (20 minutes? That must have been some cigarette!) and suggested we exchange numbers. He went off to play pool with a friend and I hung out a little bit more. I have to say that I felt pretty good. I also felt pretty buzzed. 

I hung out a little longer, wondering if my new-found superpowers of meeting people would manifest themselves again. (Spoiler alert: They didn’t.)

Eventually I decided to call it a night and head home. (Yes, it was at 4 A.M. Shut. Up.)

Next: 27 Days of Summer

Previously in TMI: Carl decides he needs to start dating again. The question is, why?

Now, I could open this piece with a story of why I haven’t seriously dated in years. But that story is messy and embarrassing. It’s full of really bad decisions and stuff that doesn’t make me look very good. You don’t want to read that, do you? I’ll just tell you about my adventures at Navy Pier last month…

Why I Haven’t Seriously Dated in Years (You knew that was coming.)

There’s a couple reasons why. At this point, one reason is really just an excuse. It’s about a guy I dated whom I was head-over-heels in love with, who broke my heart.

At this point, you’re probably saying, “Cry me a river, girl.” I know, I know. This isn’t a new story. But it’s mine. So here we go, the story of He-Who-Must-Not-Be-Named.

It was one of the few times in my life I met someone while just walking down the street. He was out with a friend of his and it was love at first sight. I mean, his friend was hot. We all chatted innocently enough and went out for a drink. We talked and laughed but I couldn’t get his friend’s attention. In the end, it didn’t matter. He-Who-Must-Not-Be-Named kept flirting with me and I began to find him incredibly charming.

Soon we were dating. What was so amazing about him was that I really had fun hanging out with him. It was a best friend and a boyfriend all wrapped up in one attractive package.

And yet…

There were a lot of problems in our relationship. Problems that I chose to ignore.

I was happy around him, but we weren’t together as much as we could have been. He was frequently “busy”. I was unhappy as I began to feel that he wasn’t as into me as I was into him.

He wouldn't stay the night with me, ever. I was never invited over to his place (because he lived with his brothers, I guess).

Hell, that's what made me sleep around while we were together. I loved him with my heart and soul, but he didn't satisfy my needs. We never spoke about being monogamous (that in and of itself was a problem), although he told me he was. Not that I asked.

He also had a sugar daddy. Sugar godfather, but same diff. He told me about it, but always with that charming smile on his face. I never got all the details and I never wanted them, but he had an older man (not a relative) who paid his endless AmEx bill.

He had a history of dating much older, richer, powerful men.

But me? I certainly wasn’t rich. And I’ve never been powerful.

I didn't sleep around to get back at him. I can say now that I did it because I knew, deep down, that this wasn’t going to work. I wasn’t able to be the man that he was looking for. It killed me that I wasn’t that man. And it hurt.

And there it is. That says it all, doesn't it?

There was lots and lots of great stuff about him. The best thing is that he taught me to be affectionate in a non-sexual way. I will always love him for that. He was my best friend. At least for a short while, he was.

It's hard to say that I would do it all over again, because the pain was the worst in my life. But maybe, just maybe, that pain isn't because of him. Maybe that pain didn't have much at all to do with him. Maybe it was just the pain of having to own up to my past, of having to be honest with myself. Or maybe the pain was just falling out of love, regardless of who that person was.

Even if that person still must not be named.

The aftermath wasn’t pretty. I made some poor choices as I decided to “sleep the pain away” with everyone who wasn’t my ex. I went back to drinking, trying to numb the pain.


Cut to, today. I’m done being all “woe-is-me”. That chapter is complete and I’m back on the block. I’m going to put myself out there and begin to find my way. I’m going to make more gay friends, start networking and even start dating (not on Grindr).

And I said that there was a second reason I haven’t been dating, didn’t I?

Here it is: I’m scared of being rejected.

There. I said it.

I hate meeting guys and getting a text message the next day that I’m not what they thought I was and it’s better if we don’t continue. I hate that some guys don’t know what they want and I get caught in the crossfire. I hate having to tell someone that I don’t feel anything.

I hate having to think that I could get my heart broken again.

And yet, here we are.

Are you ready for what’s next? Because I think I am.


Next: Baby Steps (I think so…)

Why are you reading this? Well let me tell you…

I’m a gay man in Chicago who is going back to dating for the first time in a few years. I’m in my 40’s, I (think I) look like I’m my 30’s and I make choices like I’m in my 20’s.

Something for everybody.

In this blog, I’m going to put my life out there and let it go. Feel free to read it, laugh at it, judge it, connect with it, make fun of it, enjoy it.

A couple ground rules before we get started: (1.) Names have been changed to protect the innocent (or guilty, most likely). (B.) I don’t take myself too seriously, so you shouldn’t either. (III.) I tend to write like I talk. Very casual, extra words. Horrible grammar but very casual. Just pretend we’re having coffee at your favorite place, you haven’t seen me in weeks and we’re getting caught up. And? You have strep throat, it hurts to talk so you let me dominate the conversation.

So, if you're interested in what it's like to be a gay man who dates, you've come to the right place. Pull up a cocktail, make an appointment with your therapist and refill that Paxil prescription. Get comfortable because I'm ready to start dishing about the biggest knuckle-head I know: me.

And away we go!


Spring 2012.

I went in for an annual visit with my doctor and for some reason I had a meltdown. I just burst into tears. Long story short, I was stressed out. She suggested a therapist and I followed through.

In one of my first sessions with my therapist, I spent 45 minutes detailing all the drama at my job, how I was coping, which person was behaving badly, each tedious choice I made… The poor guy had to listen to all this. He couldn’t get a word in edgewise as I detailed every godawful event from the last three months. Poor thing. Thank goodness I pay him….

At the end of my monologue, he sat in his chair, nodded his head and said, “Well, here’s how we fix this. You need a boyfriend.”

Wait. Whut?

“Yes, and why do you think that is?”

(I hate when he makes me do all the heavy lifting.) Um, because…if I had a boyfriend to focus all my energy on, I wouldn’t be replaying every event at work over and over in my head?

“Yeap!” He nodded his head up and down, raised his eyebrows and gave me that look. The look that said, “You already know this.”

And I did.

Sigh.

I haven’t been dating much for a few years. Why? The short answer is that I wasn’t ready. Why now? I’m ready. Almost.

The fact of the matter is that the type of guy I want to meet doesn’t hang out in my living room while I’m watching Happy Endings. And so now is the time for me to begin putting myself out there.

Want to hear about my drunken misadventures, dancing on a box? Interested to learn more about online dating? Can’t wait to hear about my latest blind date? So excited to read about my mis-steps in Boystown activities?

Good, ‘cause that’s what you’re going to get.


Next: Baby Steps