Too close for comfort?

I'm not quite sure what I've signed up for, but I have a feeling that this might not go so well...

I received a text last night from The Student telling me that he'll be in New York at the end of July, and asked if he might stay a couple of nights at my apartment. (I can't blame him for asking- I did repeatedly offer my air mattress through my drunkenness the night we hooked up.)

Me being the weakling that I am, I told him that he could stay for two nights and only at the beginning of that week, as I will be quite busy toward the end of the week. Whether or not he decides to definitely stay remains to be determined, but I think we all know that he won't actually be using that air mattress.

It's been over two years since I've had a boyfriend and spent extended amounts of time with a man, so I'm not too sure what I think about being in such close quarters for two straight days.

Update: Red.

So, Red resurfaced a couple days ago with an attempted booty call. I declined in a pitiful attempt to play hard to get, then reciprocated last night.

I don't think he's my Prince Charming, or even that I will know him a month from now, but I'm glad I saw him semi-sober. Although I am still trying to figure out why he slept in my bed in full body Under Armour, right next to me, and didn't touch me all night or morning long. (After we already had had sex a couple hours earlier...so it wasn't some attempt at being a gentleman. wtf is that.)

On the plus side, he rolls giant blunts, has a now confirmed super hot body, and is a very oddly sexy combo of ghetto and smart.

I was kinda hoping for a better connection, but I'm not kicking him out of the rotation yet.

I think I need to work on my choices.

I don't know why, but I do find Ivory Coast to be somewhat endearing, despite the bouts of the giggles, the rooftop incident, and the time he tried to follow me home. The first two hours of both of the dates we've been on have been really, really nice. They've also both ended with Pothead showing up, some giggles, and some molestation attempts....so, yes, I clearly need to put an end to this.

For some reason, though, I still kinda like him. I really can't explain it, and he keeps doing really weird things that are making it difficult.

Case in point: an hour ago, my phone rings, Ivory's number. We usually text, not call, but OK. I pick up.......it's Pothead. Chatting with me on behalf of Ivory, asking me to come hang out.

So, either:
a) Diana's little sexting bit the other night got them thinking about a threesome.
b) They really are secretly 14 year old girls impersonating French African men.
or
c) Pothead is secretly Ivory's agent/bodyguard, who pretends to be his friend as to not freak me out.

or d) they are just fucking weirdos.

I don't know. It's all very strange. I am thinking about all of the men I have been out with in NYC and my track record is really not looking good. I'm starting to think it's me. Full rundown coming later, maybe someone can help me figure out the pattern.

Update: Ivory

I went out with Ivory last night. Yes, even after doing the 50-yard dash out of Brooklyn last weekend, we've been texting all week and I agreed to a Sunday night date because a) I *did* have fun with him on the first date and b) my karma is all fucked up after the Brooklyn incident and I need to set it straight.

As on date #1, everything was good at the first spot, a nice tapas bar on the Upper West Side, then en route to the second...the requests to come home with me began, and continued every five to ten minutes. Now, I'm not sure when I became such a prude, but I've decided to make this one wait a while.

So...at some point I decided to share my dating secret with him. He was telling me about some girls hitting on him at school....so I nicely suggested that maybe he should start fucking one of them so that he wouldn't be so horny and we could just chill a little.

I don't think he liked that suggestion so much? He told me that he didn't want to do that, he only wanted to be with me...at which point I told him that I am not monogamous. I don't think he liked that either.

Anyway, at least I'm honest. But, I do believe what I told him. Heidi's Secret to Dating #1: Keep a fuck buddy on the side at all times.. Any woman who's woken up at 7 AM with a snoring naked 3rd date in her bed knows that sexual frustration doesn't usually lead to good places.

UPDATE:

Midwestern Boy (aka Platform Cutie) called last night. No mention of our psuedo-meeting on the 6 Train.

Phew.

Date is set for Thursday. I know, a whole five nights away. But in all fairness, I am one busy girl.