Jim, I see one problem with us being in a relationship. And it’s a kind of huge problem.

To: Pamela Beesly
From: Jim Halpert
Subject Storage boxes

Uh oh…

To: Jim Halpert
From: Pamela Beesly
Subject: Blondies

Oh, Jim! I didn’t mean it like that! It’s not big enough for me to want out of our relationship. I’m just saying we have a problem.

And here it is.

Now that we’re getting into the more personal questions of 21 Questions, I feel kind of weird asking you to tell me some of the stuff that, as my boyfriend, you should want to tell me anyway… Or at least think to tell me…

To: Pamela Beesly
From: Jim Halpert
Subject: Cleaning the bathroom

So, you’re saying that because I tell you because you asked, rather than because I wanted to, or even remembered to, it’s not as special or you don’t feel loved or accepted? I’m not really sure I got that right.

To: Jim Halpert
From: Pamela Beesly
Subject: Marilyn Manson

Not exactly. I guess what I’m saying is that part of being in a relationship is wanting to tell the other person your stuff… Not needing someone to ask before you share. That kind of thing… I just feel like we might be cheapening that a bit… Not that I don’t trust you, but when we do this game, how am I supposed to know that you wanted to tell me rather than you just felt obligated to?

Am I making too much out of this?

To: Pamela Beesly
From: Jim Halpert
Subject: Lilacs

Okay, I understand what you’re saying. But remember, at the beginning of this game we both agreed to play, which means, at some level, we both agreed that by the end of the game, we might be sharing our deepest, darkest secrets. And we were okay with that. We both agreed. So it’s not necessarily a force or an obligation to tell something, but it’s a want to. And you know if I asked you a question that you just really didn’t feel comfortable answering, I would back down.

As for wanting to tell you things… Maybe you don’t do this, but sometimes, when I want to tell you something, I’ll ask you the question I want to answer because I know that I’ll have to answer it eventually.

And, I always want to tell you everything. Did you know that?

To: Jim Halpert
From: Pamela Beesly
Subject: Fire truck puzzles

Really? I had no idea.

I guess you’re right. We did agree to tell each other everything, so it really shouldn’t matter how it comes up… And I guess your idea of asking questions is right… I just feel weird because the question that pops into my mind as our fourteenth is one that I just really don’t want to have to ask.. I’d rather you just tell me.

I just… I don’t want to be that girlfriend. You know? The one that asks her boyfriend all of the deep, penetrating questions because he’s closed and won’t tell her anything… Or because she’s paranoid and nervous, or I don’t know…

To: Pamela Beesly
From: Jim Halpert
Subject: Cat costumes

Do I have to come over there and knock you silly? Listen to me. I want to tell you my crap. Okay? I want you to know everything about me. If that freaks you out, I’m sorry, but I want you to know. And you don’t have to be afraid of asking me questions. I’m not going to yell at you and go running to the nearest bar. Do you understand that?

To: Jim Halpert
From: Pamela Beesly
Subject: Jolly Green Giants

But… I just don’t want to be that girlfriend… I want to be the one where the boyfriend wants to tell her stuff.

To: Pamela Beesly
From: Jim Halpert
Subject: Anti-perspirant

Pam, I’m not Roy.

To: Jim Halpert
From: Pamela Beesly
Subject: Expo markers

Oh my god… Jim, I’m so sorry. I didn’t even realize he’s where all that was coming from… I know you’re not Roy... I just….

To: Pamela Beesly
From: Jim Halpert
Subject: Hootie and the Blowfish

You have a really bad problem with going to the bathroom when you’re embarrassed or sad. It’s okay. You can’t help how you feel or how he hurt you and changed you. I’m just going to have to work a little harder to make you feel loved and appreciated, that’s all. And I don’t mind doing that.

You said you don’t want to have to ask the fourteenth question. Would you feel better if I just answered as many as I thought you might be wary of asking?

To: Jim Halpert
From: Pamela Beesly
Subject: Toilets

There’s just something calming about the flush of a toilet… I’m sorry. I’m so dark and twisty. I hope you can handle that.

Yeah…

To: Pamela Beesly
From: Jim Halpert
Subject: McDogs

You are not Meredith Grey… I am, however, McDreamy. You’re not too dark and twisty for me. You’re going to have to try harder than that to scare me off, Bees.

As for your answers: I don’t have any STDs. I’ve never gotten a girl pregnant. I’ve never attempted suicide or hurt myself in any way. I masturbate about 4-5 times a week (but maybe it’ll go down soon)… Um, that’s all I can really come up with right now. Did your question fit any of those?

To: Jim Halpert
From: Pamela Beesly
Subject: Butterflies

If you’re McDreamy, I have to be Meredith. Who else can I be? (And how do you know all of this about Grey’s. Is this guilty pleasure number 23231313?)

I’m glad you don’t have any STDs. I’m glad you haven’t gotten a girl pregnant or tried to hurt yourself. The masturbation stat is pretty interesting to me… Geez, Jim, why don’t you find a girl that can take care of that.

None of those were my questions.

To: Pamela Beesly
From: Jim Halpert
Subject: Chinese chicken go meow

I know about Grey’s from Kelly. Geez.

Does that particular stat hurt your feelings? You see, I’m at this dilemma, and the dilemma is that I have a girlfriend who could fulfill that particular need for me, but I don’t want to rush her or make her feel like that’s all I want from her because it’s not. And I don’t even really want to bring it up to her because I don’t want her to feel pressured just because I brought it up. But, if she asked me to stop, I think I could do it.

Then what was your question?

To: Jim Halpert
From: Pamela Beesly
Subject: Blue belts

Oh, okay. A little less creepy now.

No, it didn’t hurt my feelings. I was just playing with you. It would hurt my feelings if it was that high and we were having sex, though... And, I’m sorry about your dilemma. I’m sure your girlfriend really appreciates you not rushing her, though. It’s a big step, and if she’s anything like me, she has certain ideas about when she should have sex and with whom, so it takes her a little while to actually go at it… Not that she doesn’t want to, it’s just a big step for her and she doesn’t want to take it lightly because when she does have sex, it means a lot to her… You’re a gentleman, not wanting to pressure her like that.

And since you told me all of that about you, I feel like I should reply and tell you I don’t have any STDs, I’ve never been pregnant either (though I did have one small scare), and my masturbation stat is almost as high as yours. I have a man that could take care of that for me, but we’re not taking that step yet.

And to add to my dark and twisty-ness: As far as the hurting myself thing goes, once in sixth grade I seriously debated taking some pills, but I think it was just a hormonal rage type thing… The phone rang and jolted me out of it before I was actually going to do anything.

To: Pamela Beesly
From: Jim Halpert
Subject: Wax fingers

You don’t have to explain your reasoning for not wanting to have sex, Pam. I’m okay waiting as long as you want to, and it won’t affect our relationship if you don’t want to do it until five days after we’re married. I just want you to know that I do want you and desire you. And it means a lot to me too. But you’re exceeding all expectations of girlfriend capabilities, so it’s not taken me very long to get there.

I’m glad the phone rang. I’m not sure what I would do without you. You and your phones. Is this some kind of sick love affair you have going on? If so, I’m jealous.

Now, the question? It’s making me nervous the way you’re avoiding asking it.

To: Jim Halpert
From: Pamela Beesly
Subject: Headphones

Thank you, Jim. You really are just too amazing. And I’m glad the phone rang too. And shut up. You’re not funny. Even if I am smiling like a school girl.

Okay, the question. Question Fourteen: How many partners have you had?

To: Pamela Beesly
From: Jim Halpert
Subject: T.S. Elliot

Oh, that’s the question?

Hold on, let me count them all.

To: Jim Halpert
From: Pamela Beesly
Subject: Fargo

Oh my gosh… Is that really your number? That’s the third time you’ve counted to ten… Jim, that’s scaring me, I’m not going to lie.

To: Pamela Beesly
From: Jim Halpert
Subject: Semicolons

Hey, settle down. I was just playing with you. Remember how I said I thought sex was special? Yeah, there aren’t thirty women in my life that are special.

I count three. Brittany, my college girlfriend Andrea, and Katy.

To: Jim Halpert
From: Pamela Beesly
Subject: Coach

Three is better than thirty…

But… Katy?

To: Pamela Beesly
From: Jim Halpert
Subject: Hanging by a moment

Katy… Let’s see… How do I explain this one? No, I didn’t feel about her the way I should have to elicit sex. I just. This is hard to explain, and not exactly the way I wanted to.

Do you have any idea how long I’ve loved you?

To: Jim Halpert
From: Pamela Beesly
Subject: Christmas presents

I’m sorry, I just choked on my applesauce.

Did you just tell me you love me? Through an email? And did you say you have for a long time? How long?

To: Pamela Beesly
From: Jim Halpert
Subject: Snow White

I’m sorry… I didn’t mean to tell you in an email. Was the phone call better? I promise, I’ll tell you for real later. In person. To your face. When I get over how idiotic I was to tell you in an email.

And yeah, it’s been for a long time. What can I say? I would say since the day I met you, but I think that would be a fabrication. I’ve definitely been interested in you that long, but it was about two years ago, I guess… And then when things started moving along with Roy, I couldn’t stand it. Which is why I dated Katy. And then when Katy was ready to have sex, it just seemed like… I don’t know, maybe the easiest way to get you off my mind and out of my head? I don’t know.

To: Jim Halpert
From: Pamela Beesly
Subject: The Fray

Jim, promise me that if you ever need to get me out of your head again, you won’t go bang another girl. I don’t think I can take it.

The phone call was better. Don’t beat yourself up over it, honey.

To: Pamela Beesly
From: Jim Halpert
Subject: Underneath the covers

I promise I’ll never go "bang another girl" to get you out of my head. I’m sorry that hurt your feelings. Believe me, it hurt me too.

You called me honey.

Now, how many partners have you had?

To: Jim Halpert
From: Pamela Beesly
Subject: Oceans Twelve

Wow, so you’re the first person to know this. But, 2.

Roy and I broke up for like three weeks in college. Steven, in my Spanish class. I just wanted to have a taste of something different. DO NOT SAY IT.

Yes, I called you honey.

To: Pamela Beesly
From: Jim Halpert
Subject: That’s what she said?

Wow. You never told Roy, huh?

I like honey.

To: Jim Halpert
From: Pamela Beesly
Subject: Whoopee Cushions

Nope. I would have had the ass whooping of the century. Though I’m pretty sure he had sex.. I mean, it was three weeks, so that’s 21 days… So probably 20 girls.

To: Pamela Beesly
From: Jim Halpert
Subject: Gymnastics

He just never knew what he had. You know that, right? You aren’t stupid for loving him or wanting him to love you back. He’s stupid for letting you slide through his fingers.

To: Jim Halpert
From: Pamela Beesly
Subject: 1-800-psychic

I’m beginning to see that.

To: Pamela Beesly
From: Jim Halpert
Subject: Wheat

Want to know something? I’m really excited about our trip this weekend. It’ll be nice to have a weekend with you.

To: Jim Halpert
From: Pamela Beesly
Subject: Vaca

I’m excited too. Just remember to make a good playlist for us. We have a long drive… And you know you won’t get all weekend with me. I’d like to get to know Laura and Caitlin too, you know? Seeing as I’m in a relationship with their uncle.

God, Jim, I don’t know how we’ll ever break up…

To: Pamela Beesly
From: Jim Halpert
Subject: Scars

We’re not going to. I’m not going to leave you. I’m not Roy.

It’s already done, the playlist. You can add to it if you want. Laura and Caitlin will love you.

To: Jim Halpert
From: Pamela Beesly
Subject: Alerts

Just keep reminding me. Eventually, it’ll get through my thick skull, and I’ll be able to let go of those fears. Okay?