Posted in Dating

Date Night Overload!

So, in the after math of the confusion with the Pirate, I have a quickly filling social calendar, on a very strange week. Last paycheck was a little light, and I’ve got a week until the next one, and suddenly I was supposed to have a date tonight, another on Monday, and I’m “hanging out” with the Pirate on Tuesday.

I was so certain that the Pirate was done with me that I reinstalled my Tinder app. There were 2 gentlemen I’d been talking to before I deleted the app, and I reconnected with them. One of which says he is looking for just friends, as he is just getting through with his divorce.

Believe me, if he decides he wants more than friends, he’s going to have to show me signed divorce papers!

I’m not going through another debacle like I had with the Bartender ever again! That was miserable, and not really worth it. All it’s done is make me more susceptible to that pistanthrophobia that I wrote about the other day. 


He’s asked me out for Monday evening. He originally wanted Tuesday, but the Pirate’s already claimed that day, and, unless he decides he is done with me, he gets first choice.

What can I say? I really do like the Pirate! I had gotten rid of my Tinder app, but when he asked me to give him space, I’m so used to that being the beginning of a brush off that I re-installed it and am now going on dates again.

Sort of.

I don’t know really what the Pirate’s end goal is. He tells me he doesn’t have one, and he uses specific phrases like asking me if I want to “hang out” on Tuesday, instead of asking me out. Hanging out, I think, implies that we’re just going to chill at his place.


No, not “Netflix and Chill” (though I wouldn’t be opposed to that option), just chill.

I’m still in that nebulous place with him, where I don’t know what he wants or what he’s after, but I know that he’s apologized the two times I’ve gotten really upset at him for not recognizing that I’m a person with needs and feelings. Plus, he’s been trying to fix the things I was upset about:

  • He’s been actively not interrupting me (though I’ve been guilty of interrupting him a time or five).
  • He told me he doesn’t like talking on the phone, and yet we’ve (two nights in a row) talked on the phone for over an hour: almost two hours the night before last, and last night I had to be the one to end the conversation.
  • He’s asked me about myself and things in my life a little bit more. Asking my opinion instead of just focusing on himself.
  • And when I told him that the “you’re smothering me/I need space” conversation usually means the guy is about to get rid of me because he’s gotten what he wanted, he told me that that couldn’t be farther from the truth.

That seems like a good sign to me. Like maybe we’re moving in a direction, a positive direction…

But I’m afraid to get my hopes up.

Hence, I’m still on Tinder.

Tonight I was supposed to go out with the Professor. The one who smokes cigars… I had that same feeling I had when I went out with the Marine. I decided it was probably a bad plan. He invited me to a place I haven’t been before, which already made me nervous, and it’s got an outdoor cafe, which also made me nervous. I think I look weird out in natural sunlight, and I fully expect people to notice my flaws more when I’m in natural light as opposed to the man-made light in a bar or restaurant.

Also because it’s a place I’ve never been before, I was nervous about the cost. I know technically he’s supposed to pay, or probably would have paid, but I hate going out to a place where I’m uncertain if I’ll be able to pay my own bill. I don’t like to assume that the guy will pay for me, and I’m kind of broke this summer…

I spent a lot on gas the last few weeks just hanging out with the Pirate, and the food thing last Friday, while AMAZING, was way out of my way a little bit.

Did I ever share pics of that?

Delicious and so much fun!

And we got to keep our wine glasses!

Back to the point, though: I’ve spent more money than I should have from this paycheck, and so I’m not confident that I could pay for myself if he were to have asked me to do so.

Not that I think he would, but it’s an added stress when I’m already not really comfortable.


The guy I’m seeing on Monday (the one who wants to be just friends) is also a high school English teacher, so we have something in common that we can discuss already. He also just got back from a road trip to see family, so he can talk while I get comfortable with the situation, whatever the situation may be.

Plus, he has a really good reason for not asking me out right away. He was going out of town, and he even told me that he liked my intelligence, so as long as he didn’t scare me away before he got back, he wanted to actually meet with me… at which point he told me he wasn’t looking for a relationship because it was too soon after his divorce.

All positive things to say. At the time he was telling me this, I think the Pirate and I had gone out twice, so there were no expectations, I wasn’t feeling guilty about talking to someone else, and this guy just wanted to be friends, so it was not a big deal at all.


The Professor, on the other hand, isn’t clear with his intentions.

I don’t know if he’s looking for friends, or a hookup, or a girlfriend, or a wife… or just a good conversation. I find that last to be doubtful. The conversation thus far has been spotty at best, without a real explanation as to why… granted there was at least a week long window where I’d deleted Tinder because I was frustrated with it, and was spending most of my dating time with the Pirate anyhow.

But I matched with all three guys at about the same time.

The Teacher (boom, nickname accepted) was fun and a little flirty, but more actually into conversation, which was nice. Then he let me know he was going to disappear for a bit, but friends was all he was really after anyhow, so it works. Haven’t seriously spoken in a while, but his grammar is on point, and he let me know today he was back in town and wanted to get together.



I don’t feel like I’m doing anything wrong by meeting with him, although I think I’ll need to tell him that probably friends is all it’s ever going to be… He’s friendzoned because the Pirate is pretty awesome. Maybe… maybe if we’d have met before he went out of town, things might be different, but I don’t really think so.


The Pirate was the first to act, and has been the most attentive… and is by far the most attractive. Probably also the most zany as well, but I like that. I’m not 100% comfortable with him yet, but I have to admit I’m moving at a more healthy pace with him than I have in the past. I feel comfortable at the pace we’re going, and it’s okay that I don’t know the end goal, because I like where it seems to be going.

A friend told me I could re-evaluate things at any moment, and that was okay. I just need to know if the Pirate is still someone I think is worth the effort, and I do. If that ever changes, then I have the right to say something, and don’t have to feel guilty because, contrary to my inner fear, I have NOT been unintentionally leading him on. I’ve been working towards something, and if it doesn’t work, then I was still trying, and so I’m not guilty of being a horrible person.

Does it make me nervous because I don’t know if he’s ever going to want something from me? Yeah. A lot. But it feels like we’re moving in a positive direction, and since I’m not 100% certain of anything, as scary as that is for me, I’m getting comfortable with it.

I think more than anything, there’s this fear that if I go out with someone who’s not clear of their intentions, like, for instance, the Professor, I’m going to be worried that I’m jeopardizing the potential something with the Pirate.

Or maybe that’s me trying to logically explain why I really am not interested in the Professor even though, on paper, he’s got a lot of the “right” qualifications.

He’s a professor, which proves he’s intelligent.


He drinks wine, which potentially means he has good taste, and also means he enjoys the finer things in life. It could mean he likes to pamper himself… or it could mean he’s a raging alcoholic who’s poison of choice is fermented grapes. Who knows?

My friend, the Olde Man, would tell me it means he’s pretentious as hell, and I think that from his IG photos, that’s the vibe I’m getting and I don’t like that. Maybe that’s why I’m not really into him.

Or maybe it was his hesitation in asking me out.


The Pirate didn’t hesitate at all. Asked me out to meet him the day after we matched. The conversation was awkward in spots (poking me in the side, talking during the movie, talking for a very long time about sex after the movie), but there wasn’t a hesitation, and he’s continued to try to see me since. With the exception of the miscommunication surrounding the smothering comment, he’s been pretty much full steam ahead right along with me.

Even the Teacher didn’t hesitate to show his interest, though he quantified it and explained why it would have to be postponed. He complimented me on my intelligence, and touted that as the reason why he wanted to meet me. There was never any mention of my looks, though, as I’ve mentioned before, there is at least one photo on my profile that shows how ample my bosoms are. Many of the guys who swipe right do so only because of that one picture, so for him to compliment my intelligence first definitely gets him bonus points.

I think that pretty much settles it: I am just not into the Professor! I guess it’s a good thing I had a good reason to cancel the date…

Now, if I could just figure out if the Pirate is ever going to want something serious so I know whether or not I can give the Teacher a real shot… assuming that’s an option, of course.

Ugh… dating is so complicated!



High school teacher by day, relationship/romance blogger by night. Help me add author to the list. Vote for my book idea here:

One thought on “Date Night Overload!

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s