J: Cruisin’ with the 'rents

I’m sitting in an airport waiting for the flight that will take me to Miami and the start of my family’s Caribbean cruise.

This one is with my parents and my brother and I’m doing my very best to be excited about it. But the thing about family vacations when both kids are still single is that they can quickly rewind the clock 20 years and bring out the worst in everyone. It would be different if I was doing this with a husband and a kid….or just a husband…or even just a *boyfriend*. At least in that situation, I would still be seen as an adult by my parents.

But, we’ve never been on a cruise before. And it’s been a very very long time since our last family vacation. So, who knows, it might be fabulous. It might also be extremely frustrating.

I am planning to spend time with the family but I’m also really, really hoping for a nice “Love Boat” experience. It could happen, right? I hear that they have tons of singles events on board and surely other single guys who were dragged along will be looking for a little holiday romance as well, right?

And, luckily, I’m not sharing a room with my brother (although he will be next door…with the ‘rents just across the hall.)

I’ve had my November date and it’s not quite December yet so this would purely be a ‘bonus’ opportunity in regards to this challenge.

Who knows…anything can happen if I keep my mind open.

I specifically brought my computer along for blogging purposes....even though I won't be logging in due to the per-minute cost on the ship. So, while there will be some radio silence for awhile, hopefully I'll have a bunch of posts for you when this vacation is done.

Wait...or maybe I should hope that I don't blog at all since I'll be too busy having fun and won't have time to be on my computer at all.

Fingers crossed, friends...fingers crossed.

S: November Cup Update

And we have a winner!

The November Cup has been taken by Contender the Third!

At the start of the race, C3 had worked his way into the lead by being the only contender to have actually made mention of a social outing. And, only a few laps in, this contender earned a decisive victory by suggesting dinner early next week.

We went a few rounds about where we would eat, because I’m notoriously bad at choosing a restaurant, but the message exchange was actually quite fun. He plays along very well and we feel the same way about a lot of food related topics. This is promising for dinner conversation. We’ll see if he ends up being any better at in-person bantering than the last two Misters.

After the flurry of exchanges to get our plans hashed out, I found myself disappointed that there wouldn’t be more to discuss. What do you email about once the date has been made when the original intent of your messages was to get a date made? I didn’t want our exchanges to come to a screeching halt. I was having too much fun.

Good thing I’m a master of random crap. I threw out some odd topics of conversation and the banter continued. Until now. Because he left town for the weekend.

And now I kind of miss Contender the Third. The newly crowned Mr. November. I found myself looking forward to his responses to my random crap. He takes the bait I put out for him and he makes me laugh. And then sets out new bait for me.

I’m actually looking forward to our date as more than just a quota filler after the last week of back-and-forth. I didn’t feel a great connection during the group drinks last week, but now that the ice is broken and it will just be the two of us, perhaps things will flow a bit better. We both have a better sense of what can be discussed safely with the other and we have a little bit of shared history to get us going.

And wine. There will be wine. And martinis. This will definitely take the edge off. But not too much. It’s good to have a little edge. It’s much easier to keep one’s distance when sober.

So that’s it. The November Cup has been decided. I was sweating this one, but a worthy stallion has come through.

In a late breaking photo finish, Contender the First also suggested a get together for drinks not a couple of hours after I accepted Contender the Third’s dinner request. I’d rather have Contender the Fourth cross the finish line for December, but it looks like I’ll be able to keep C1 at the starting gate for an early take-off next month.

Then I have to figure out what to do with the remaining contenders.

S: The November Cup

I just checked the calendar…we are halfway through November. This worries me because I have yet to score any date plans. And I’m not sure I will. This month is running low on weekends and one of them is a holiday. Scheduling options are getting scarce.

I have a few Mr. Possibilities I’ve been working on, but I don’t know if any of them will hit the “go out” button in the next couple of weeks. Every one of them seems close, and yet…nothing. And I’m still in this place of feeling like I can’t do the asking because I think it makes the subsequent “I don’t want to get involved” chat more difficult. I mean, why do the asking if I’m not interested? How do I explain that?

So it’s going to be a race to the finish this month. Here are the 3 contenders for the title of Mr. November. At this point, they are neck-and-neck. And I may get left in the dust.

Contender the First -

There is a fella I’ve been exchanging messages with on my chosen dating site. He started the conversation by letting me know he was amused by my profile. Not the first time I’ve heard that, but if a guy says it in an interesting way, I’ll respond. He seems intelligent, can banter and hasn’t made any overt, disrespectful sexual remarks. My tactic with this contender is to keep encouraging talk of food preferences we have in common in order to work my way into a lunch or dinner invitation.

There are two major issues with C1. First, he’s still married. He’s listed himself as “separated.” I don’t know what this means, but right now I couldn’t be more done with dealing with Bitter Divorce Guys (BDGs). (To be fair, I haven’t yet sensed his bitterness, but I have yet to meet a divorced guy on the dating scene who isn’t). And if he’s not even actually divorced? He’s all kinds of potential train wreck. But, all I need is one date. One dinner and a kind “I can’t see getting involved while you’re still married and dealing with this crap.” Just one. This month. Like…now.

The other issue, you ask? He is currently out of the country. Yes…you read right…*out of the country*. Just as I was working my, get-him-to-ask-me-out-and-make-sure-he-thinks-it’s-his-idea magic, he sends a message saying he’s getting on a plane and crossing the pond. Great, I’m trying to get a date on the calendar in the next couple of weeks and he leaves the country. The good news is that he sent me a message from over seas. I was surprised by that effort. Definitely a sign of interest. I guess we’ll see what happens when he gets back. Just need that one date. You know…yesterday.

Contender Uno may be lagging behind the pack due to his relative proximity to me and any place we might go together.

Contender the Second -

There is another fella I’ve been conversing with on the same dating site. I sent him a random message a while back and finally got a response apologizing for the delay in reply. Again, just like Contender the First, he seems intelligent and fun to banter with, but I’m not that excited about him. He corrects me. Don’t correct me. That’s just rude. We have some grammar pet peeves in common, which gives us something to chat about, but I can’t deal with hanging out with a corrector. You spend too much time wondering if you’re saying the wrong thing and if he’s judging you. And then you have to try really hard not to correct in response to his corrections.

BUT, I just need the one date. It just doesn’t seem like he’s going to ask. We exchange friendly messages, but he doesn’t seem in any hurry to meet. He asks me what my plans are for the weekend, but then doesn’t really take it anywhere from there. I’ve started to believe that he will not be asking me out in time for him to be Mr. November. If at all.

Which, in reality, I don’t mind. I’m not very interested in him. Actually, if we did go out, I think the lack of spark/interest would be mutual. I think finally I would find myself in a situation in which we both know it’s not going any further and we’ll both be fine with it. (Also, I suspect he may be writing a secret blog about dating too…he’s not the dating site type.)

Even so, Contender the Second is picking up the rear with Contender the First at this point, due to his lack of a sense of urgency.

Contender the Third -

This contender has been added to the roster by more traditional means. He’s my second fix-up of the Date Club Challenge. Guy was the first fix-up, although a subtle one. Ok, he was more of an ambush, but I’m paying the price for it, so I don’t feel bad.

Anyway, a friend suggested a fix-up between me and a guy who works in her office and I told her I was o.k. with it, knowing full well I need to get a November on the books. So, she set up an after work drink get-together between the three of us and another friend. It went well. He’s a nice guy. Very congenial and polite. The four of us had some good conversation over some drinks and appetizers.

Buuuuut, no spark. My friend called right after, and before her phone died, I told her if he asked me out I would go, but that I didn’t feel any strong sparks flying around. Frankly, if he didn’t ask me out, I’d be fine. But we didn’t get to talk much, so maybe there’s more there.

Here’s the little bit of news she passed on to me during our brief post mortem chat…he’s getting divorced. Like, right now. His divorce is final this week. Again, he didn’t behave like a BDG, but he’s going through this as I type. He can’t be in a good place.

I suppose this isn’t a bad thing. It gives us both a safe reason not to get involved. No need to reject anyone personally. We have an “out.”

Back to the race. Contender the Third moved to the head of the pack today by being the only one to actually have suggested a social outing together. As is the modern custom, C3 friended me on Facebook a day or two after our fix-up and began a conversation. We’ve been having some fun going back and forth for a few days and both playing the “how can I create an ask-out situation without going out on a limb” game. It’s working.

I got a bit concerned when he said he was out of town for the next two weekends and how did December sound, but then he also added that we could possibly go out during the week. I made a push for during the week.

Place your bets on Contender the Third. He’s a few lengths ahead.

BUT WAIT! Another stallion has just entered the race.

Contender the Fourth –

The very thoughtful dating site will sometimes send me mate suggestions. Most of them are frightening. This one was not. This one is tasty. And he sent me a message. Yay! I do like hearing from the tasty ones.

He has some catching up to do and I’m not sure he’ll make it, but he does seem interested. He’s younger than I’d like. And, if we go out, I could see him being a bit cocky for my tastes, but he comes across as a nice guy in his messages and hasn’t gotten creepy yet. And no sign of a divorce.

And did I mention the tasty? Yum.

I don’t imagine he’ll catch up to the other contenders at this late date, but he might. He certainly has the confidence to. I won’t have to do a lot of encouraging. This is not a contender who gets shot down.

If he doesn’t win the November Cup, my bets are definitely on him for December.

So, the race is on. Four contenders. Two weeks. Can Sheila pull this one out or is she going to owe Mr. Piggy? Put on your best hat, sip your mint julep and sit back and enjoy the show.

J: Free

Done.

After much, much stressing and a very difficult, much longer than it should have been discussion, I’ve finally broken up with Mr. October.

He’s willing to slow way down. He’s willing to give me all the time I need. He’s willing to just be friends. Anything, anything, anything I want, just so he can be in my life.

I suck.

I’m supposed to call him when I’ve had time to think about it. I’m supposed to call him when I figure it all out. I’m supposed to contact him when I’m ready to go out again…as a friend or ‘hopefully more’.

And…ouch…doesn’t that plan sound familiar?

It’s not going to happen. I’m not going to call. I can’t go there emotionally and it’s just not fair to him to let him think we could be friends, knowing that he would always want it to turn into more.

Ouch…that sounds familiar too.

So....moving on!

In other news: now that Mr. October can’t think it’s because I want to be exclusive with him, I also dumped OKCupid tonight. Yes…my profile is officially down (at least until I log back in again, which I don’t see happening any time soon.)

I have a couple of prospects for December. Hopefully one of them will work out without the assistance of a free (crappy) online dating site.

So long, OKC...you brought me nothing but heartache!!!

Two breakups in one night. No more Mr. October. No more OKCupid.

I feel free. I feel relieved. I feel like a jerk.

J: Chicken Shit

I suck.

Just called to cancel my date with Mr. October. But I wasn't able to find a way to have 'the conversation'.

I texted my bestest guy friend to admit that I chickened out. His response: "Jane...you should have done it last week."

Yeah. I know.

The sad thing is...I think Mr. October knows too. He avoided any "I must see you" type of comments...which meant that I didn't really have an opening to go into my prepared "we're not in the same place" speech that I was planning to launch into from there.

He did ask me to call him tomorrow. I owe him this conversation. Maybe I'll figure out how to just blurt it all out by then.

Why am I feeling so trapped by someone I've only gone out with twice?

J: Breaking up...again

Yaaaaay.

In less than a month, I get to have my second break-up discussion.

Fun.

After only two dates, three phone conversations and a handfull of texts, Mr. October has completely, totally and absolutely fallen for me. And while so much flattery is nice, I just can't bring myself to pretend anymore.

He called yesterday to tell me how excited he is about seeing me on our date that was scheduled for tonight. Apparently, instead of going to a local movie theater where you can get dinner while you watch your movie, he wants to go to dinner and then to a movie so that we can spend even more time together. He also expressed his interest in seeing me as much as possible and at least "more than once a week". But I'm leaving for a cruise with my family (I'll be blogging about this soon, too) on Friday and my calendar is pretty much filled up for the rest of the week with other pre-existing plans and last minute trip preparation tasks.

If I were actually interested in him, instead of making excuses about how busy I am, wouldn't I have found a day, an evening, or even just a spare hour to see him before I left the country for over a week? I didn't even really want to give him my email address when he asked if we could stay in touch while I'm away. I just didn't want that much of a 'responsibility' while I'm on vacation. Plus, quite honestly, I wouldn't be all that upset to find myself in the middle of a little on-board romance.

Unfortunately, when I woke up this morning, it was pretty apparent that I'm finally succumbing to this cold that I've been fighting off all week. Fortunately, Mr. October knows from yesterday's phone call, that I'm not feeling my best. So, while I know that it's not going to make him happy, I'm going to call and cancel our date for tonight due to the level of crappy that I'm feeling. I'm also going to take advantage of being on the phone with him to tell him that while I really and truly enjoy spending time with him we're just not at the same place. And I don't see us getting there.

I know where I went, emotionally, with Mr. September despite the fact that he wasn't able to go there with me. And it's just not fair to let this 'relationship' progress any further when I can tell that Mr. October is already headed down that same path. He is a great guy...but we're not going to turn into an "us"...no matter how much he wants it and pushes for it.

This sucks.

I have a feeling that the actual event of breaking up with myself last month will have turned out to be a whole lot easier than the event of breaking up with Mr. October will be...even if the aftermath was (and still is) harder.