Ask Dr. NerdLove: The Back-Up Plan

Dear Doctor Nerdlove,

I don’t know what to do. About half a year ago, I started hanging out with these two girls that lived a few floors down from me named, Jane and Lynne. I thought their roommate was cute, so I started hanging around their apartment. Although that didn’t work out, I ended up getting to know her roommates and we became really close friends. In fact, they are two of my best friends at the moment and I see them almost every day. However, there are issues with between myself and both of them that are beginning to strain the friendship I feel.

Lynne and I are very close. She’s a very fun and intelligent woman (one of the smartest I’ve ever had the pleasure of meeting). I consider her boyfriend one of the luckiest guys on the planet. During the first month of our friendship I had a crush on Jane and Lynne was often the one who I would talk to about it. After just a week of talking, she had helped me plan out the perfect date and set me up for the perfect opportunity to ask Jane out. Unfortunately, Jane ended hooking up with another guy within that same week. At this point, Lynne and I had gotten so used to each other’s company that we would see each other every day and talk for several hours at a time.

Now as a personal policy I view taken women as off-limits, but as we spent more and more time together, I started to develop feelings for her. Around three months ago, it ended up coming up in a conversation and I told her that if she wasn’t with her boyfriend of three and a half years, I would want to be with her. To my surprise, she told me she felt the same way. I ended up talking to Jane regarding this and she revealed that she has had her eye on me since the first week I’ve known her. In fact, Jane even went so far as to say that I was “oblivious and stupid” for not noticing and that she’s always felt weird talking to me alone because she felt like she was “stealing from Lynne.” Ever since then, she’s been talking about breaking up with her boyfriend, but the last time she got close, she couldn’t go through with it.

Here’s where it gets complicated. According to my other friends and Lynne, Jane has taken a liking to me as well. It was actually kind of obvious to me even. She acts affectionate and playful towards me a lot of the time, and she likes to touch me. Not in a sexual way, but she likes to hit me or grab my hand. Anyways, my other friends encouraged me to ask her out, even though I thought she would say no. Even Lynne agreed with the idea, which I have to say hurt a bit. While I do not like Jane as much as I like Lynne, I finally gave into peer pressure and asked her out. As I expected, she said no. When I asked why, she said that she wasn’t what I wanted and that she couldn’t give me the affection I want.

Ever since then, things have been awkward and I’m afraid I’ve screwed the pooch on this one. Both Lynne and Jane have acted different towards me ever since. While Jane is already beginning to treat me the way she used to, I’m scared of losing Lynne as a friend. She hasn’t been acting any differently, but she hasn’t been coming up to see me as often. When we do see each other, I feel like something’s different or that she’s mad at me. At this point, I don’t know what to do. I think I upset her somewhere along the way, but I’m afraid if we talk about it we’ll say too much if you catch my drift.

Six of One

Hoo-boy. You need to be getting on your hands and knees and thanking whatever deities you believe in that I seem to be unable to spontaneously develop the power to reach through the Internet and slap the stupid out of you.

You, my friend, don’t seem to know that you’re supposed to quit when you’re behind. When you’ve realized that you’ve dug yourself into a hole, you stop digging. As it is, you have done goofed. Big time.

Dr. NerdLove’s Rule #43: You gotta pick one.

((Dr. NerdLove’s Rule #43a: You don’t necessarily have to pick one, but you’d BETTER have some serious game, son. And a fallout shelter when it goes wrong. ))

Here’s a hint: trying to go for both girls without alienating everyone only works in Archie comics and that poor sonofoabitch is never gonna get past second base. You keep flip-flopping between the the two girls like a bad sitcom. As soon as you get shot down by one, you go back to the other. Three goddamn times going by your letter.

To be perfectly honest, I’m kind of astounded that either of them are still talking to you after the first time you decided that that no, you liked Lynne, no wait, you liked Jane, no wait…

So you like Jane. Fair enough. You missed your window of opportunity because you were too busy trying to set up the perfect moment. You – and many men like you, including myself before I wised up – don’t seem to realize: there is no perfect moment. There is this moment. That’s it. Waiting for the perfect moment is just an excuse to chicken out.

Dr. NerdLove’s Rule #5: He Who Hesitates, Masturbates. Alone.

Because you were so busy hemming and hawwing, some other jerk comes along and, critically, doesn’t hesitate and he gets with Jane instead. Fair enough, shit happens, and even if you had made your move, you may still have gotten shot down. At least you would’ve had closure but still. Bygones.

So instead, you develop feelings for Lynne, your new best friend. The one who was “safe” because she was taken. So instead of playing games, you were straight with her. You were your real self. You felt confident around her. Hell, you made a goddamn move… kind of. But hey, this one seems to have gone better. Shit, you’ve even found out she’s been kinda interested in you from the beginning and this is part of why Jane said no.

(Side note: I don’t care if you’re a man or a woman, you can’t call dibs on people. I don’t give a damn who saw them first or how long you’ve had a crush on them. If you want somebody, you rolls the dice and you takes your chances – otherwise they’re fair game for all and sundry.)

But hey, now Jane’s back and being all flirty and you’re getting confused. Well, here’s a free clue for you: sometimes people like to flirt. Maybe Jane was missing the attention you were lavishing on her. Maybe Jane’s jealous that Lynne’s getting your attention and she’s kind of an asshole like that. Doesn’t matter, because you apparently believe that your dating life is an open democracy.

I’m sorry, but peer pressure is the worst excuse I’ve heard for a boneheaded mistake in a long time. I realize you’re young but if you asked a girl out because everyone else told you to, I hope you’re looking forward to spending the rest of your life as Marty McFly’s dad… before the timeline where he pimp-smacked Biff.

Let’s be honest here Six: it was because Lynne didn’t break up with her boyfriend. You were hurt, Jane was being all flirty again…

As a result, you decided to pull the worst mistake anyone in your situation could have: you decided to switch Door Number 2 for Door Number 1. And since dating isn’t Let’s Make A Deal, you ended up with nothing.

You know why?

Dr. NerdLove’s Rule #27: Nobody likes to feel like they’re your contingency plan.

By going after Jane, you were telling her “Enh, you’ll do,” which is incredibly insulting to her. “Baby, you’re totally the girl I want… assuming that this other girl says no first.” is not the key to a woman’s heart.

Then, just to add insult to (Lynne’s) injury: you say you knew you were going to get rejected in advance. So not only did you hurt Lynne – who you supposedly have feelings for – but you hit on someone knowing that she was going to say no anyway. So for all intents and purposes, you tossed Lynne’s feelings aside for no good reason.

“I think I upset her somewhere along the way.”

Ya think?

SPOILER WARNING: of course you fucking did.

If Lynne isn’t mad at you, I’m going to be fucking amazed. She’s well within her rights to hate you with the passion of a thousand burning suns. I’m goddamn astounded she’s still willing to talk to you at all.

You want whatever chance you have to save your friendship? You want to know what you do?

You man the fuck up and apologize to her for being an asshole. You’re gonna have to talk about it and you’re gonna have to just risk “saying too much” because you owe it to her to let her scream at you for being a selfish bag of dicks. If you’re especially lucky – and you’d better hope that God really does look after fools and Irishmen – she won’t bludgeon you with something heavy. And when she’s done screaming, crying and screaming at you some more… you back the fuck off. She’s going to need time and distance to heal – and decide how she’s gonna deal with your dumb ass.

Oh, and you don’t get to date Jane either. Sorry. She’s Lynne’s friend too and your trying to hit that is just going to be another reminder of just how much you fucked up. She’s not your intermediary. She’s not your spy. You don’t get to use her to try to find out what’s going on with Lynne or to use her as your go-between to pass messages.

Look, I know I’m being hard on you, but you’ve gone and needlessly hurt two people – one of whom is your best friend – because you can’t stick to your emotional guns. And there’s no guarantee that there will be any saving your friendship. It’s going to take a long time for things to recover – if they ever do. The only thing you can do is wait.

And be less of an idiot next time.

Settle something for me, Doc:

Digging into the spank bank when your with someone. Wrong or right?

– My Girlfriend Would Kill Me

There’s nothing wrong with jerking off, regardless whether you’re in a relationship or not. The only time it’s a problem is if you’d rather jerk it than actually have sex with your significant other – and then the problem is likely in your relationship.

Don’t forget: I post bonus Ask Dr. NerdLove questions over on the Dr. NerdLove Facebook page. If you want to weigh in on these relationship questions, be sure to join up and keep the conversation going.