So. Lets expound upon HS. I mentioned him briefly earlier in regards to re-connecting with a group of guy friends from HS. HS is now known as TheSinger. Since he has a habit of singing (sometimes just loudly humming) along with the radio, theme songs, background music.

TheSinger and I were friends in HS; we actually dated for about 3 months. I was 15 or 16, infatuated with the idea of an older man (he was… 22? 23?) and he was very sweet and smart. Worth nothing that I then (and now) generally preferred older men, which lead to my other friends referring to my dates who came with “walkers”. 23! Walkers! Oh har har. I’m still a li’ salty about that.

Anyhoodles. So. TheSinger and I didn’t work out in HS because … well, no one’s fault. I realized I just wasn’t that interested in him. Nothing to do with him, it just wasn’t… sparking for me, no zsa zsa zsu. It was a fairly amiacable breakup, we still hung out with the same group. Well they hung out together and they continued to let me tag along (I was the young one amongst them).  And then we all reconnected over this past summer.They saw me go through not being with NiceGuy to being with him, to not being with him.

One night in the midst of while NiceGuy and I were not together, but on our way to being back together – I was on the phone with TheSinger making dinner for him (NiceGuy, not TheSinger). In the midst of the convo a pot started boiling over, so I got off the phone rather abruptly. NiceGuy showed up shortly after and as TheSinger and I weren’t in the middle of a scintillating conversation when I abruptly hung up, I didn’t think to call him back. Which lead to him texting me the following that night “Just so you know, I’m not trying to date you”.
*scrrrr wha? I had thought no such thing, and responded with that, letting him know things were cool. That I had just gotten caught up with dinner, then company was over and said company was probably there all night, so… yeah. I didn’t call him back. No big deal. I was slightly taken aback that he needed to clarify but was okay that he did because then I knew we both were on the same page: The Friend Page.

Fast forward to this past weekend. Now, TheSinger was constantly after me to hang out, which, okay, I am awesome. And he seemed to be the planner of the group, arranging hikings, wine tastings, etc, so I thought nothing of it. Until this past week. My January’s schedule was absurd, and I knew there was no socializing in there for me – so we’d talked about hanging out in early Feb. Did our normal thing – dinner/tv. He intro’d a new (to me) tv show that I fell in love with and he left. Still on the just friends page. But the next day, I get texted asking to go to a concert. Out of the group, I’m the only one in town, so I figured he just needed company; I already had plans and couldn’t make it. So  he gets another one of the guys. That, combined with recent… something, a feeling I had, I had wondered if he was angling for a date. But he asked one of the other guys. I tell myself to stop overthinking and my ego needs to knock it off Disarming.
Another one of the guys, Tech, was having a board game party this Saturday(which both Tech and TheSinger mentioned to me) but I had babysitting duty that night.

I get a text from TheSinger on Friday, asking what time I’m babysitting and telling me to come to the party then go babysit. Well, I wasn’t up for drinking then watching someone else’s kids so I declined.
He texted me the day of the party telling me to come after, but it would be late, so again no.
Then he texted asking when I was done, he’d stop by my place for a nightcap since I missed the drinking there. Well, still no clue how late, so again, no.
I was texted on his drive home, asking me to go to a wine tasting the next day. This next day being Valentine’s Day, and he made no mention of anyone else joining us. I am again starting to overthink and wonder… I again decline because I’ve already got plans with my kittens (shopping: 2 pairs of new heels, a new wallet and a Happy Valentines Day present to me!)

I hear from him rather consistently on Sunday, but still tell my ego to knock it off and pipe down. Monday is President’s Day, a free day we have off at my company. So I sleep in until *cough*1:30. And lounge around, do practically nothing, and fall back asleep at 7:30ish. I wake up at 10:45 pretty foggy brained and planning on showering and then back to sleep. I check my phone, just in case. Four missed texts (within 25 minutes of each other). A call (two hours later). A voicemail. All from TheSinger. I shoot him a text to let him know I wasn’t just ignoring him, I’d been sleeping. He calls. At 10:45 at night. I’m still mostly asleep and hoping to stay that way.
I know somethings coming, but we both make chitchat, and then bam. He asks what I think about going out with him. Note: he does not ask me out on a specific date, but asks what I think about us going on a potential date. I turn him down (see above: still no spark, no zsa zsa zsu) and mostly, I’m just kinda surprised… and if I’m honest with myself, a little disappointed. I couch my response in terms of still recovering from NiceGuy, which while true… I also know I had seen the end coming with NiceGuy and I am ready to date someone. I just haven’t met anyone I’m actually interested in getting to know more about. I also bring up how I don’t want to date someone from within a group of my friends again. I know that my breakup with NiceGuy isn’t what caused the destruction of the Circle of Trust (our ol’ group), that destruction had been on its way for awhile, but without NiceGuy or I to keep it together… the Circle is now just Arcs.
(heh. geometry humor, my HS math teacher would be so proud!)
TheSinger and I chat for a little while longer, and then I plead off – still hoping to shower and get back to bed and sleep before 12. No such luck, I was awake till 3:30 in the morning.

I had wondered after his strong (and seemingly out of nowhere) “am not interested” text if it was a case of him protesting too much, but had been willing to take it at face value and kept things friendly. There was no overt flirting, no leading on (at least to my eyes) and yet, he felt enough of something there that he wanted us to go out.

The next day I had a text from him, wanting to know about maybe setting up a recurring event, where we could hang at his place and watch some tv/eat dinner. This rapid fire turnaround immediately put me in this frame of mind:
A) he was never that interested and is more than willing to go back to being just friends.
B) he still IS that interested and is trying to be just the best gosh darn guy friend evar.

I let him know my schedule won’t allow anything recurring like that, and that it kinda feels date-y to me. So maybe we shouldn’t, just for a little bit. He doesn’t understand how its date-y now, when it wasn’t before. I explain its because he put the date on the table, whereas before it wasn’t even a possibility. We were friends. This entire conversation has taken place over text. Its at this point he asks me to call when I’m headed home so we can chat. So I do, begrudginly, because I kinda hate having to explain myself. Especially when I think its possible I’m going to hurt someone. Hopefully within*that conversation, I finally got through to him that even tho I said no and we have never gone on a date: the parameters of our friendship have changed.

He has expressed interest and I’m aware of it (now). I feel that I have to re-judge how hanging out with him will be it. Its no longer two buddies. Its a girl and a boy. And said boy, wanted to date, to kiss, to get, the girl. That changes things. I hate that it does, but it did. I know he was hoping that it wouldn’t. But, it did.