I Am Everyone's Fool.

That’s me, dear readers. And I am caught up in a vicious cycle. I am guarded because I have been let down before. Then someone challenges me to open up. I struggle with it, but I give in and put myself out there, because although hesitant, I believe that one of the times that I do I won’t be let down. And then I am let down.

Most of the time I brush off the feelings of disappointment, but every now and then I feel like a real fool. Like when I’m giving someone an umpteenth chance to prove me wrong reject me. Like I am feeling right now.

Despite agreeing to meet up with Hobbes, I only believed we would actually meet up for the briefest of moments after we had outlined the plans. I switched back over pretty quickly when I didn’t hear from him for two days around the time he was traveling out here.

The cancellation came in two parts. The night before he bailed on the “maybe” portion, because he could not say no to (free) dinner with family friends. He thought he’d still be able to meet with me after. I asked him if we should just cancel our plans then, or whether he wanted to keep the suspense going?

I wanted to cancel them myself, you see, but if I waited for him to do it so I could write him off forever with a perfectly clear conscience. I wasn’t surprised by the official cancellation, mid-day the day of our plans, but I was pretty blown away that he didn’t mention anything that sounded even remotely like he was sorry that he wouldn’t be seeing me. Or that he felt bad about doing exactly what I had said he would do.

I guess I had thought that after I had made such a big deal of not wanting to be bailed on that Hobbes wouldn’t have made plans if he didn’t think he could keep them. That if he made them anyway and then had to break them, for whatever reason, that he would have done so with an apology. That he would have felt bad. For me. For my feelings.

All Hobbes wanted to know was whether a rain check was possible. I think no. No rain check. No future plans. No emails, no IMs, no texts. No more going out on a limb.

And no thank you to whatever you, dear readers, might think are words of encouragement on this subject. I'll be walking this one off alone.

Will You (Hypothetically) Go Out With Me?

About a week ago I was invited out by Hobbes. Yeah, remember that guy? I’m sure all romantic interest between us is over, but he’s pretty fun to chat with so we still do that every now and then. In one of those conversations I had asked him about whether my spring trip would coincide with ski season, since I would be in Denver visiting friends and wanted to get some skiing in, assuming I could find someone to come along with. He mentioned that he would never turn down skiing, and I said I believed him, but that I also would never make plans with him again, ever.

He seemed to think that was pretty harsh. Let’s see, we had tried to meet up in Denver and in Chicago, at least once – and sometimes twice – a year, over the course of four years, and not once had we been successful. Yep, the Universe had made himself clear: Hobbes and I were not going to interact in person, and there wasn’t anything either of us could do to change that.

Hobbes clearly thought I was overreacting since he went on to hypothetically ask me whether I wanted to meet up when he’s going to be in Chicago for work. I responded fairly negatively, so he suggested I mull it over.

I don’t want to mull it over. I want to not have been presented with this scenario. It’s a Catch 22.

If I say no, the stars will align and he will be in Chicago, and I will be free, and then I will be that girl that’s too afraid to put herself out there to meet up with a guy she still talks to even though she hasn’t seen him in years.

If I say yes, the meeting will fall through. Maybe his trip will get canceled, maybe he’ll have to work late, maybe he’ll be in the burbs and traffic will be so terrible due to 12+ inches of snow it won’t make sense to keep the date (we did, after all, just have a blizzard). Some part of me will get excited about this meeting, even though I don’t think it’s likely we’ll actually get to the meeting part, and then that same part of me will feel bummed about it after. I’ll also feel really stupid, for not knowing better.

I told Hobbes to ask me again closer to this hypothetical visit, but we all know I’m going to make myself available in the end. Hypothetically, anyway.

Lost in Translation

I never finished my Hobbes tale, mostly because I was really saddened about what had happened the week leading up to when we were going to meet up. It was something entirely different than I had thought. And it was worse. So here goes.

Hobbes had gotten a terribly mismatched impression of who I am. He’d been reading the blog as if it was me, talking to him, which of course is not what this blog is. This blog is a journal of my dating (mis)adventures, but it’s an edited journal. I write about things that I think are funny or interesting or insightful, and a lot of the time I write about the feelings I have as I’m having them. These feelings are not to be mistaken with my true feelings, which usually take some time to figure out, and which would have been explained to him directly if and when it made sense to in our relationship.

What I felt first was a tremendous sense of loss. Hobbes no longer thinks we are relationship compatible. And perhaps we aren’t, but I know that his sense of that isn’t based on a true understanding of who I am. I feel responsible for his confusion, though, and his sentiments are very difficult for me to absorb. Did I do this to myself? Did my desire to weave an engaging tale on my blog undermine the budding of a real relationship and hurt someone I care about?

I often have doubts about whether I should continue writing a blog about something that is so personal to me. I am concerned that I over analyze situations that I want to write about in order to tell a good story. I am worried that I misrepresent my true self by capturing all my fleeting and fluctuating emotions. I think it’s entirely possible that writing a dating blog is detrimental to my success at dating.

Underneath the sadness, though, was a lot of “grow up Hobbes”. True, when he told me he was no longer interested in me romantically I told him the good news was that he could keep on reading the blog. I am flattered that he did so. And yes, I probably should have thought more about how awkward it would be if he was reading it while we were actively talking about meeting up. He’s a big boy, though, and I assumed that if he chose to read the blog that he would have done so with eyes wide open. He doesn’t have to like what I think about his actions but I didn’t misrepresent them. I wasn’t passive aggressively trying to tell him things through the blog. And how could he not have expected to see something negative about himself?

Most importantly, I was disappointed that when he thought he was seeing a different version of me on the blog than in our emails that he didn’t say something to me about it, instead of coming to all these conclusions about what I expected and what I thought.

I tried to explain it to him over email. About the blog; that it’s not all true, but it’s not all false, either. About how he was taking it way too literally and should know better. And I apologized. I never meant to hurt him and I was truly sorry that he was feeling the way he was.

He wasn’t interested in me explaining in person when I was in his hood… I told him I really wanted to see him, to apologize and clear things up. He responded that it wasn’t that big of a deal.

Message received, loud and clear.

"I'll Think About It" Means "No"

Well, dear readers, who knew what a saga this whole Hobbes thing would turn into? Certainly not me. Despite being dismissed for the love of his life (who he’d been pining for, unrequited) I told him I still thought it would be fun to grab drinks as pals this Friday. My reasons, I assume, are obvious:

• I want to know whether I feel a romantic attraction to him. This would come in handy in 4-6 months, should he and his lady love no longer be involved, and our email chatting resumes. I could save myself a lot of time (and a plane ticket) if I already knew whether I wanted that chatting to be platonic or romantic.
• I want him to think he’s made a mistake. Once he sees and interacts with me in person I think he’ll seriously consider why he cast me aside so easily. I am very engaging in person.

What? I’m not going to feel bad about that, besides, I’m the one who was cast aside, remember? I get to act a little bit spurned. I digress. I sent this email Monday, and after two full days he replies back that his week’s been crazy! My email is already 3/4 of the way down his inbox! Then he says he’ll think about it and get back to me.

Um, excuse me? If you have to think about whether you want to spend approximately 90 minutes with me over a beer this Friday, which had been planned for weeks, and which we talked about still doing as friends last week, then you don’t want to. What is there to think about? His reasons for bailing, I assume, are obvious:

• He is really, truly no longer interested in me. Not romantically, not as email pals, not anything.
• He’s afraid that seeing me will make him doubt having kicked me to the curb in favor of his new lady love. This one sounds a little self-centered, but potentially valid.
• His new lady love doesn’t think it’s a good idea, probably because of concerns that #2 would happen. This would be ridiculous. She just told him she liked him SEVEN days ago.

I have half a mind to simply take myself off the table. That would spare me the frustration of waiting for his reasoning as to why we shouldn’t meet, and it would save him the presumable agony of trying to explain himself. I’m sure his response will imply my feelings are being hurt. You know what? They kind of are, but mostly because now I feel jerked around. And, as we just reviewed in the rules, you shouldn’t make someone wait.

I am waiting, though, and I do want to read what he has to say, assuming that he responds at all. As it stands it’s been a full 24-hours since he replied and we’re just over a day from when we would be meeting up.

Time is running out. And so is my patience.

You Could Never be Better than Her… I Hope You Understand

long distance emails
possible romantic match
he loves someone else

Ohhh, I knew it! I was completely spot on with the fall off in communications with Hobbes. Today I get this email that basically says he’s in love with someone else (and has been for a long time) and although she hasn’t been interested and/or the timing was off she is definitely interested, now, and so he’s going to pursue that.

He says he’s sure I’m bummed and this might be a surprise to me. Bummed? Maybe a little, but like I said I wasn’t sure whether we’d click romantically and we do have a bit of a distance issue. Surprised? Please, if I’ve learned anything in my dating adventures it’s that my gut is unbelievably accurate. I think I called this about a week ago.

He also says obviously we won’t be meeting up when I’m out there in a few weeks, since it wouldn’t be fair to lead me on if there’s something possible with someone else. Honestly? I think we could meet for drinks regardless; he can be honest about his romantic availability (or lack thereof) and still meet me for friendly drinks.

But this email feels more like I’ve been kicked to the curb. Even though he says he enjoys chatting with me and would be up for continuing if I am it’s abundantly clear in his email how his feelings for this girl obliterate any feelings for me, entirely. I 100% believe that he’d have sent the same email if this girl’s change of heart had happened after we had met up, no matter how great a time we might have had. That part stings a little, especially given some of the exchanges he and I have had as of late, but I don’t have any hard feelings. I certainly wish him the best.

I wish me the best, too. It does seem a little unfair, though.

Calvin’s Dad: The world isn't fair, Calvin.
Calvin: I know, but why isn't it ever unfair in my favor?

The Week in Review | 01.18 - 01.24

Hobbes
Things have cooled off there, I think. I can’t put my finger on it, exactly, but there’s been a decrease in communications and more than once I feel like my response to something was disappointing to him. Stupid stuff, mind you, like movie references, but it’s hard not to worry a little that maybe the more he gets to know me, the less he likes me. The most damning evidence? He asked for my number over a week ago but never used it.

My gut (and my Magic 8-ball) isn’t usually wrong about these things, but I do have a tendency to over analyze so I‘m not putting much stock into it. Yet.

An Older Vintage
I’m starting to notice a trend in my online dating adventures… I only attract older men. Men between the ages of 39 and say 45. As a reminder, I’m 31, so this puts the dudes interested in me a solid 10 years my senior. There’s not necessarily anything wrong with a 10-year gap, but this gap in particular I think crosses dating age groups.

With this older age range, I run into a couple of issues that in and of themselves aren’t necessarily bad, but can present additional hurdles earlier in the dating scene. I don't need extra hurdles.

Like relationship status. The older one gets, the more likely one has been married previously, which for me means I at least need to cover the basics of what happened there. And then again, not being married (but wanting to be) at 40 begs the question “what’s wrong with him that he‘s never been married?”

And the children question. Ideally I would like children, all of which would be birthed before I turn the ages these men already are. Some of them aren’t sure whether they want children, possibly because the older you get the less likely you’ll be having them, and some of them already have kids, which is a whole different bag of worms. Even those that definitely want kids sort of freak me out - they could be on a much faster time line than I am.

I would never let an age gap stand in the way of a great relationship, of course, but all this older interest begs the question... what does the fact that no one my age wants to date me say? About me?!

Something Unexpected

One of the downsides to being self-aware is, well, being aware of your self and what you’re thinking. I have always had a processing delay in my feelings, it typically runs anywhere between 12 and 24-hours when I’m presented with a situation I wasn’t expecting. For the last few days I’ve been mulling over my current situation with Hobbes, and I have come to the conclusion that I will just have to let things play out. In other words, I have to wait. I hate that.

What’s weird about it is how even though I’m thinking about it a lot, I’m not experiencing most of the anxious feelings I normally do. I don’t think emailing novel length emails every day is too much, I don’t think IMing hundreds of lines during a good portion of the work day is too much, I don’t think talking on the phone is too much, either.

I have all those early relationship feelings. Excitement when I see an email, disappointment when I don’t. That small smile when he asked how he would go about calling me this weekend (since we had already deleted each other’s phone numbers).

I feel like I should tell him. How much I enjoy spending this virtual time with him. I haven’t though, not directly. I don’t want to get ahead of myself, because I’m going to see him.

That’s right; I’ll be in his area visiting another friend in just a few short weeks. Our schedules only overlap for a small period of time, and although we’ve been unsuccessful every time we’ve tried to meet up since he moved (about 2 1/2 years ago) I think we are actually going to see each other this time.

I feel remarkably calm about the whole thing, reason enough to be alarmed given my history. We didn’t meet up in the past for a lot of perfectly good reasons, but I know at least I’ve gone away from those situations feeling a little deflated, more hurt than warranted given how we weren’t ever communicating regularly when these opportunities presented themselves. This time, though, there’s a lot of lead up. Our conversation is way past surface, there's a pretty steady undercurrent of flirtation and we’ve discussed that we both have some level of expectation and/or active interest.

It all seems totally natural to me… which is exactly why I’m worried.

He’s going to read this post, because I didn’t tell him I was writing it and not to read it (although I thought about doing that), and that doesn’t really bother me, either. I sincerely hope there is vodka nearby when my feelings about him kick in, good or bad.

Busted.

Six months after I started this blogging adventure, and barely a month after I gave thanks that no one I had written about had found the blog, it happened. Someone I had dated, who I had written about, busted me. He emailed me (which we sometimes still do), saying he had come across my blog and was "intrigued". Before I even had a chance to decide how to respond - do I tell him about the post he’s featured in? - he wrote back this: oh, so I am TOTALLY Hobbes!

And he is. Fortunately he was not featured in a Failed First Date or even worse, a Worst Date Ever, I wrote about him in the post How Long Should You Wait for The Spark?.

In my response I included this ridiculously run on sentence: “This is new for me. I feel a teeny bit awkward but mostly I think it's funny and I hope you don't feel bad about what I wrote and also thanks for reading and saying you like it.” What am I, twelve?

Better back and forth email ensued, in which we mostly talked about... his hair. He describes his previous, longer hair as cringe-worthy. I thought it suited him, actually, but now he’s sporting a shorter, more professional do, and also, a beard. I always did like emailing with him, never could tell where the conversation would lead us.

Back on the topic of having an open window into my dating life, he went as far as to say “Honestly reading it has made you more endearing because it demystified what little I knew about you personally and made you more human with some of the same struggles and insecurities that I have. That any of us have.”

I’m not sure about being mystifying, but he’s definitely onto something. I used to hide the things that made me feel insecure or uncomfortable from even my nearest and dearest. I felt embarrassed, I guess, and thought it would change, in a bad way, how they felt about me. As it turns out, that's crap, and writing this blog has helped me open up about everything that affects me, flattering or not. Through it I’m becoming more comfortable with who I am and that’s bettering all my relationships, not just my dating ones.

He offered to not read the blog, but it honestly doesn't bother me. I‘m glad that he gets to see who I am, if only in my dating realm. I think I'm starting to prefer the honest and upfront approach. Maybe I'm not busted, after all.

Oh and since he’s clearly not sure why I nicknamed him Hobbes in the post, it’s because of his old email signature: It's a magical world, Hobbes, ol' buddy....Let's go exploring! [Bill Watterson]

Let’s go exploring, indeed.

How Long Should You Wait for the Spark?

Every so often you come across someone who doesn’t really seem like he’s your type but you can’t deny there’s a connection of some sort. Take this guy Hobbes, for instance. We met through a CL post and had a really interesting, engaging email conversation that I was really drawn into. We sent multiple emails daily that really felt like we were talking to each other, instead of just sending disjointed collections of information about ourselves.

I was somewhat hesitant to meet him in person, afraid I‘d be let down given how much I was attracted to him online. We did meet, though, walking around the loop mid-day with coffees. It was a different kind of date - I actually took off during work to meet him - and while I was definitely still attracted to him as a person, I can’t say I had that romantic spark.

He pursued me. We continued emailing regularly and met for drinks and dinner. We had a good time, but I still wasn’t sure if I was physically into him. I had a vacation scheduled and at the end of the last date we went on we clearly should have kissed, but by then we almost had this awkward physical barrier between us so we hugged instead.

When I got back from vacation we met up the very next day, and we did kiss. It was good… not amazing but definitely promising. For me there was still a twinge of awkwardness, the physical aspect of our budding relationship just didn’t come naturally.

I wasn’t sure what to do. I certainly enjoyed his company, and we had been on several dates, but I just don’t think I was into him, romantically anyway. It was so depressing! I had finally found someone I wanted to spend time with, but not make out with. This really isn’t something I encounter often.

HOW LONG SHOULD YOU WAIT FOR THE SPARK? You don’t want to short change yourself and possibly miss out on a great relationship, but you don’t want to lead anyone on either. My married friend says until she kissed her now-husband she didn’t really want to kiss him. So it all boils down to the kissing, then.

I think you should give the kissing two shots, just to be on the safe side. I never got to the last ditch kiss attempt with Hobbes, shortly after our first kiss he announced he was probably moving across the country at the end of the month. It didn’t seem worth it to figure out that I liked him if he was leaving, so we went our separate ways.

When you a find a connection I think you need to give a real chance, even it means some awkward or bad kissing. Besides, what's that saying about finding your handsome prince? Oh right, the frogs.