And the neurosis sets in

College Ed dated his ex for six years, which was, verbatim from his mouth, "probably four years too long." Then, as if he regretted the implications of what he had just said, he added, "But don't get me wrong, that's not to say she isn't fantastic."

Present tense: is fantastic.

A couple of months ago, before anything between us ever happened, College Ed went out to interview for summer internships in San Francisco and took an extra day to enjoy the city. While chatting with him about this at the bar the night before he was to leave, I asked if he had anything in mind that he wanted to do on his extra day.

He said no, but then added, "Well, I am going to have lunch with my ex-girlfriend." I gave him a quizzical look, not sure of how to respond, and so I asked, "Is that a good thing or a bad thing?"

"Well, she wants us to get married..."

And I pushed a bit more, "And how do you feel about that?"

He replied, "Yeeaah... no."

At the time, I didn't know which ex this was. I knew that he dated a girl we both knew in college, and that they'd continued dating after college, but I didn't know for how long nor if he has had other girlfriends (and thus ex-gfs) in the seven years since college.

The new information of his college relationship lasting 6 year (!!!) came during our conversation about timing, along with the fact that he has now been single for 2.5 years.

So, his ex-girlfriend of six years lives in San Francisco. He thinks she is a fantastic girl. She is still in love with him and wants them to get married.

Could all this talk of timing be because his lunch with her a couple of months back went really well, and he wants to keep his options open for a summer out in San Francisco rekindling things with her? He wouldn't need to invest any additional time and energy - he presumably knows her deeply well after six years together. And she is perfectly positioned geographically, being in the city already where he ultimately wants to end up.

And this was the point when I got neurotic. I googled her, looked her up on LinkedIn, stalked her on facebook (for once, I'm actually friends with someone that I want to stalk)...

And I found out that she and College Ed became facebook friends in February of this year. I know that at one point a few years ago, they were listed as being in a relationship with each other on facebook. So this means that their breakup was bad enough to have warranted a de-friending at some point. And now, 2.5 years later, they've had enough time to heal and decided to re-friend each other on facebook.

2.5 years is enough time to heal, but is it also enough time to have realized that perhaps there really isn't anyone else out there with whom they'd rather be?

And what better time to answer that question than a two-month revisit of old times while both in good ol' San Francisco?

I know I am being neurotic and making up stories. But the more I think about it, the more sense it makes to me, and the more I am convinced that this is exactly College Ed's thought process when he told me that the timing for us is just horrible. And also his thought process when he asked me why we didn't try this six months ago.

Six months ago, he still wasn't facebook friends with the ex, let alone talking to her, having lunch with her, and considering getting back together with her.

Nevermind that I have nothing to base any of this off of. But don't they always say that the gut feeling of a jilted lover is oftentimes the most insightfully correct?

Two ships, four weeks

I know enough of "He's just not that into you" (those six words are really all you need to know) to know that he just wasn't that into me.

Except each time that I'd decided to move on, he would enthusiastically email me to set up a time to hang out, or put multiple exclamation marks behind his endorsement of a dinner date, or make me smile by picking out the green-colored card during our board game because he noticed green to be my favorite color.

But then I wouldn't hear from him for a whole week. The typical set of mixed signals and roller coaster rides.

Until tonight when I just asked him what it all meant, because mixed signals don't help me.

He told me I was right to have sensed hesitancy because he is indeed hesitant. He's worried about timing because we will both be gone for three months this summer, and he fears he will simply sit and over-think reasons that this would ultimately fail during that time. Even three months from now when he will be back in Boston for one more year of school, he always envisioned himself moving to Silicon Valley after school, whereas I would continue working in Boston. And he promised himself he would not pursue another long-distance relationship.

Which is funny, because that was my exact thought process. Except my conclusion was that I was still willing to give it a shot because I've not met someone this fantastic in a long time. His conclusion was that the timing just wasn't right.

He's just not that into me.

I told him that one of the reasons I'm particularly bummed is that he is the first person to really excite me in a long time. "There are plenty of people out there to date," I said, "and most are perfectly nice, but no one has excited me for a really long time." He agreed, saying that I make him feel the same way, whereas most women don't excite him either. But he can't get excited about "us" yet because he doesn't actually know me deeply and doesn't know us as an entity and thus can't have faith that we are the two people who would be right for each other.

"So how do you get to know that?" I asked.

"By spending time with someone, by actually dating them, by investing energy and effort to really get to know their personality and person. But all of that takes investment, and I'm generally hesitant about investing because I know I will be gone from Boston in a year, and it feels horrible when something you've invested so much in fails. I'm scared, and I'm commitment-phobic because there's no stability in my life right now."

I could have asked him how he knows this would fail without even trying? I could have said that if this were really a priority for him, he'd be willing to make the investment because he wouldn't want to live with the regret that he passed up the opportunity on "the one."

But I didn't say any of that. I just said that I already figured that's how he felt.

And then he asked, "Why didn't we try this 6 months ago?" suggesting that it could have made all the difference, could have given him enough faith while apart for the summer to stay engaged and optimistic, could have been enough time as opposed to starting a relationship come September.

Talk about more mixed signals in a conversation to clarify mixed signals.

"I didn't think you were interested," I answered, and then after a pause, "and I probably wasn't ready 6 months ago." I should have told him it was because he didn't make a move. I was ready in February, if only he'd made a move.

There are so many things I didn't say that I could have said, but perhaps it's better that I left them unsaid. I could have called him out and asked why he would keep leading me on if he has had these doubts all along? Or forget all along, "Why, earlier today, would you have invited me on a 3-day hiking/camping later THIS week when you are so obviously so hesitant??"

But then I'd just be making him verbalize everything that I already know. I could have said that I've thought for some time now that I would ultimately end up in the Bay Area after a bit more time in Boston to be closer to my family and to work the East Coast out of me. Or that I would be willing to move out to the Bay Area with him after he graduates in a year because that's just what I do: go out on a limb to make something I believe work (that, or give too much to relationships and try too hard, dragging them out way past their due date).

Or I could have simply said that I think we would have amazing adventures. Which I truly believe we would.

But I didn't say any of that. What would have been the point? I'd just be countering all of his excuses and cornering him to offer new ones.

He continued.

"You are someone my unmarried self would always go on a date with."

I could have asked him what exactly that meant, and why must he still continue to give me mixed signals even within this conversation, but I didn't.

And he continued.

"But I think I would just be hesitant about this whole thing, and the summer would generate more of a wall for me. You don't deserve that."

I chuckled and told him that was the best reason that he'd given so far. He asked why.

It's because if this were a priority for you, all the timing things wouldn't matter - you make your own definition of "bad timing." It's because if this were important to you, you would think the circumstantial difficulties are just that: circumstantial difficulties that we could work through. But all of this is moot because you are hesitant. I can offer counterpoints for all of your reasons about bad timing and long distance, but I can't counter your hesitancy about "us" because that is the one thing I can't change. Which makes it the best answer yet.

He lamented how hard this problem is because there are no solutions - we are just faced with the worst possible timing. So I offered a solution, "Should we just go back to being friends?"

"Yeah I think that would be best," he said.

We looked at each other, smiled, and nodded. I smiled out of sadness and nodded in agreement because what else can I do but to agree? Perhaps he smiled out of nervousness because I smiled, but his nodding broke my heart a little bit more. He is resolute, and this was the solution he wanted all along but didn't have the balls to say.

Then he asked, "Can we still get brunch together in the fall?"

I sighed. "We'll see."

What I should have said was, "What? Seriously?" But I didn't.

Older men

Mr. Lawyer and I met at the neighborhood coffee/ice cream shop. I'd been going there daily to write my thesis with ambient background noise and had made friends with Mr. Religious, who'd been working there scooping ice cream since last May in a mission to soul search after taking 5 years to finish divinity school but then deciding it wasn't his calling after all.

One day in our neighborhood ice cream shop, Mr. Religious introduced me to Mr. Lawyer as one of the earlier investors of the shop as well as being a hot shot local criminal lawyer who only took on ridiculously hard murder cases. Mr. Lawyer was striking in appearance definitely. Despite being mostly grey (but sexy grey in the Anderson Cooper way), he had bright blue piercing eyes, a toned physique, a firm handshake, an international man of mystery air about him.

He was clearly old and obviously rich if he had the money to be a serious investor 20 years ago. During our conversation, Mr. Lawyer kept referring back to a gorgeous black woman sitting nearby with her friend. She looked about my age, and it later became apparent that this woman was Mr. Lawyer's girlfriend. And they met 8 years ago at a gay bar a few blocks down the street.

Oh Cambridge.

Fast forward a few weeks. I'd stopped going to the ice cream shop to work for various reasons but dropped in this Monday afternoon to finish some work and to borrow their free wifi to take care of a few things online.

Mr. Lawyer came in for a cup of tea (he gets anything he wants for free anytime, a perk of being an investor I suppose) and spotted me at the central table working. We both recognized each other, so he stopped to chat. He told me about his summer travels and also his plans for getting married.

"Oh! Congratulations! I had no idea. This is the woman you introduced us to last time, right?" Leaving out any qualifiers because the only one I could think of was "the *very young* woman". But yes, it was her.

He eventually had to leave and go back to work, but first needed to speak with the owner of the shop in the back office. So we shook hands, made nice, and I said maybe we'd run into each other again at our favorite neighborhood coffee/ice cream shop.

Five minutes later, on his way out the door from the back office, he came by again and asked, "Do you like baseball?"

"Sure, I like baseball just fine."

"Would you be interested in going to a Red Sox game tomorrow?"

"Haha, sure, I'm always up for a Sox game. I'll wear my hat!"

We decided to meet up at the ice cream shop the next day and walk over to Fenway together. I rushed and got there a few minutes late, but he still wasn't there. Just as I thought I was getting stood up, Mr. Lawyer with his sexy greying hair walked in the door, all smiles.

We grabbed some tacos by Fenway before the game started, and since it was pouring rain outside, we ate the tacos at the dive bar hoping to avoid getting drenched as much as possible by the time we get to the game.

A very drunk guy came up to us while we sat eating our tacos, eyed us, and asked, "How old are you two?"

"I'm 49," said Mr. Lawyer. The guy looks to me.

"I'm 28."

"Wow, he must be reeeeally good then," the guy went on, glancing over at Mr. Lawyer, not exactly in an admiring tone. Then he turned to Mr. Lawyer and started on a rampage.

"You're sick. You're a piece of shit. You good for nothing son of a bitch. What the hell are you doing out with someone HER age. YOU are a failure." And the rampage got more crass the more he got into it. Mr. Lawyer's reaction the whole time was just to nod his head and say things like "you betcha", "you're a real winner".

I guess there wasn't much Mr. Lawyer could have said to defend himself seeing that he is soon getting married to a 30-year-old woman. The drunk finally left, but not before telling us that he gets to go home and f- his wife, who's only five years younger than him. Mr. Lawyer seemed taken aback, but handled the attack calmly and well. He is a lawyer, after all.

We left the taco place for Fenway, but by the time we got there, the game had been canceled on account of rain. Mr. Lawyer asked if I'd be up for a drink somewhere instead. Never one to turn down drinks, I said sure.

The thought crossed my mind at some point that this felt potentially not quite right. The whole episode of Mr. Lawyer asking me to the game, our meeting up and walking together to the game, the tacos beforehand, the drinks to replace the rained-out game, it all screamed DATE. Except Mr. Lawyer is grey, 49, and getting married soon... to a woman only two years older than me.

Conversation over drinks was ... great. He doesn't drink, and I only had one beer, so it wasn't the alcohol smoothing things over. Somehow my recent stalker incidents came up (a story on its own that I will have to remember to tell), and that started us down a path of talking about relationships. No, that's not true. The relationship gate was opened earlier in the evening when he asked if I had a boyfriend. Always one for keeping up calm appearances, I mentioned having ended a very serious relationship a year ago, and so now I'm not in any real rush to start a new one.

I eventually finished up my beer, and we walked back to the ice cream shop where we'd met up earlier and started to say goodbye when he interrupted.

"I don't necessarily want to end things on an awkward note, but I just want to make sure I'm honest about everything."

"Sure, what's up?"

"I'm really attracted to you, if you can't tell. And it obviously can't lead to anything because I'm getting married, and she'd castrate me."

So why bring this up? He claimed that he wanted to make sure there weren't any undertones of unknown tension when we hang out, so he wanted to get his feelings out there. But he also asked if I feel the same way, and I just didn't know how to answer that. I guess I feel the same way as I do with most guys with whom I can have a great conversation - he's nice, but there's a mental block that's preventing me from jumping his bones.

In Mr. Lawyer's case, he's 1) getting married, and 2) 49.

In Kix's case, he's overly cynical, and I don't need a repeat of Broadway (Kix is another story worth telling).

So I thanked Mr. Lawyer for speaking his mind, reiterated that I always welcome honesty and stabbing the elephant in the room (can College Ed get some lessons in this?), and that I was flattered, but avoided answering the question of how I feel.

He said that he'd love to continue hanging out (hmm), as friends (hmm), and maybe he and his fiance will have a BBQ at their place or something, and he'd love for me to come over.

Hmm.

Humanized, now what?

Most of it was in my head, but not all.

I wasn't about to initiate contact with College Ed after a horrible rejection experience, and we went on for a week without communicating. Agonizing, humiliating, want-to-crawl-into-hole demoralizing.

A week passed, and he contacted me. "I asked about dinner tonight last week, but just realized that I didn't follow up. Would you still be up for it?"

All conventional wisdom points to saying no, but I didn't. I dragged myself out, debated whether or not to have a "talk," any "talk," about how agonizing the last week had been for me. But this was two days before my thesis defense, and I really didn't need additional emotional turmoil.

Turns out, he tries to kiss me at the end of the night before we parted. I, not about to assume anything this time, stood stoically thinking he just wanted a hug. But he went in for the kiss and got the corner of my mouth (I didn't move, so did he change direction last minute when sensing my lack of movement?).

Oh, so he IS actually interested. I pulled him in for a second kiss, on the lips, but just a peck. Awkward.

That was last Tuesday night. He came to my thesis defense Thursday as well as part of the evening celebrations. We went on a proper date Saturday night, and I stayed over.

That's actually a lot of seeing each other over the course of one week. And he became humanized. He has a lot of problems.

He's another guy with anxiety issues, though not as clear and not as willing to admit to them. He is extremely passive and has a hard time talking about things explicitly, naming the elephant in the room so-to-speak. He seems really hesitant on relationships, and I don't get the sense that it's because of me.

But mostly, the anxiety is so obviously a part of him, a part that a regular once-a-week friend would have a hard time picking up. So he hides it well. But I'm intuitive, and I'm not afraid to call him out.

I emailed him Sunday about the next time we might hang out. No response.

Men.

crash & burn

We hung out last night: dinner, ice cream. As we were sitting in a street-corner park eating our ice cream, a group of people started an impromptu foursquare game nearby. So we joined in for a while.

At the end of the night, he hugged me goodbye. I leaned in for the kiss, but he turned so I got cheek instead.

"I don't want you to get sick! It's not worth it."

This one really did feel like an excuse. I don't know what happened. I thought we had a good time.

roller coasters

I still haven't seen College Ed. He canceled our "date" last Tuesday because he got sick (or "sick" depending on how cynical I'm feeling), and then had an insane week before heading out for a family wedding this weekend.

Email evidence for "he likes me and wants to date me":

"I'll tell you more when I see you" - when he canceled Tuesday afternoon, using "when" versus "if"

"I disappeared... sorry I went awol" - on Friday. Your guess is as good as mine for his motivations to apologize. I wouldn't have thought twice about it - seemed to me like a natural "wait period" in between dates.

"What does tomorrow night look like for you?" - tonight, presumably asking me to do something tomorrow night (Monday).

Evidence for "he might be just being nice and has second thoughts all the time":

He got sick, or "sick" and canceled our "date".

He sucks at responding to email. I emailed back within an hour tonight tonight saying that I am free anytime tomorrow. I heard nothing more.

He's picky. Why would he pick me?

----

When he canceled last Tuesday, I wasn't myself. The cancellation destroyed me for hours. All I could do was to sulk and to complain and rant to whomever would listen. Eventually, a friend had had enough.

"Seine. What the hell are you doing?" he said. "I have never seen you like this. Get your shit together."

"I haven't been like this for a long time. I don't overanalyze or overthink about boys. Boys are boys, and I thought I'd grown out of my crazy phase about boys. But it turns out that I'm still as crazy as ever. It's just that the crazy's had no chance to come out because it's been so long since I've liked a boy this much."

"Okay, I get that," he said, "but you've got a thesis to write. Get your shit together."

So I biked home from school to get some fresh air, and convinced myself down from the crazy ladder.

In the end, College Ed is just another boy. If he likes me, he likes me. If he wants to date me, he wants to date me. If he doesn't, he doesn't. No amount of craziness or overthinking on my part will change that about him.

So that's where I am now: cautiously progressing with no expectations, ready to pull back at any second and call it "just friends." We might see each other other tomorrow night, but I'm not holding my breath so that if we don't, I'm not destroyed again.