DEAR DR. 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

DEAR SIX OF ONE: Oh man, SOM, 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: If everyone involved isn’t poly, then you gotta pick one.

Here’s a hint: trying to go for both girls without alienating everyone only works in Archie comics and that poor SOB is only killing time before they both get tired of his s--t. 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.

But as I’m often saying, he who hesitates, loses.

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, s--t 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. S--t, 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 it’s totally fair game for anyone else to make THEIR move instead.)

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 a--hole 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… in the timeline where he HADN’T cold-cocked 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 f--k ing did.

If Lynne isn’t mad at you, I’m going to be goddamn 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 f--k 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 Hell off. She’s going to need time and distance to heal – and decide how she’s gonna deal with your dumb a--.

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 f--k ed 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.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I’m 24 and male, mostly interested in women, and I feel like I’m in a weird place because I’m having trouble finding a committed partner. I feel like I’m a bit behind, and I’m not sure where to go from here.

I have a degree, I’m working towards my dream career, in my dream city, I have many friends, skills, and hobbies, and on the whole, the only thing that seems missing is a loving, committed partner.

I seek it out, and I do find connection, good connection even, and yet after a few dates, it always seems to end. They’re too busy, or they aren’t feeling it, or I’m not feeling it, and I’m back to square one in a month or less.

I feel almost “behind” in this respect, as I have old friends from college with years-long relationships, and others who are more committed and stable in this area of life than I am, and it feels like I’m doing something wrong. I do research connection-building quite a bit, but it hasn’t quite gotten me where I want to be yet.

Some would say I’ve not yet found the “right person,” but it really feels like I have, but it’s been the wrong time, or it’s my fault for not presenting myself “right.” I was also kind of an awkward nerd as a kid and into college. I didn’t have my first girlfriend until I was 22, and that lasted only two months, my longest relationship to date, and I was a virgin until 23, and I’ve never had sex with a partner, only a few casual encounters here and there. This makes me feel worse, because I feel like I’m not getting anywhere in building romantic relationships with others, and that frustrates me.

I guess my questions here are along the lines of “how do I do better?” How do I get myself in a place where I find partners trying to build something like I am? I try to date when I can, and seek out people I can talk to, and enjoy getting to know, but it seems like I’m still not quite getting it right…

-Too Old for this S--t

DEAR TOO OLD FOR THIS S--t : One of the most perversely fascinating aspects of my job is how arbitrary some things can be. One of the most obvious examples is the idea that there’s an age where you “should” have had a partner or a relationship already… and past that point, you’re simply going to be locked out. Because women — and, let’s be real here, I mostly see this from straight dudes — can tell that a guy missed the window. Somehow. What’s fascinating is that tripwire is always, always that person’s age minus one to five years. I have seen people who’ve convinced themselves that the fact that they didn’t have a girlfriend by fifteen meant that they’d missed their window.

The thing is: there’s no such thing as “too late”. The vast majority of women out there aren’t demanding your dating resume; they’re not gonna ask you to explain this large gap in relationships or why you’ve had so few. What women care about is finding a guy they like, who they connect with and who makes them happy; the number of partners he may or may not have had before her is ultimately meaningless.

By that same token, I see plenty of people who worry that they’re “falling behind” somehow… such as in your case, TOFTS. They look at other people — friends, family members, total strangers — and think that those people are somehow a marker of where they should be. Which is, honestly, the dumbest possible yardstick I can imagine. It’s one thing to say that you would prefer to have had X experience by now or that you wish you’d done Y already; that’s understandable. Those are feelings, desires, things that are personal but not definitional. However, when you start using words like “should”, or comparing yourself to other people, all you’re doing is introducing unnecessary misery into your life.

Here is a truth: using other people as your measurement of where you “should” be or what you’re “supposed” to be is a recipe for heartache. The problem with looking at anyone else and assuming that they are the exact model you should be following is that, frankly, you’re not them. They have an entirely different life than you; they’ve had different experiences, grew up with different parents, had different friends and had completely different challenges and opportunities than you did. The only way that you could legitimately say that you were “falling behind” would be if you were living their exact same life, at the same time and getting different results. But you you didn’t. You’re living your own life, separate, independant and unique from everyone else. You can’t measure your life by anyone else’s, only your own.

Here is another truth: the fact that other people have had long-term relationships — for suitably variable definitions of “long term” — doesn’t make them better or more advanced than you. It just means they have a relationship. Having a relationship isn’t a marker of maturity or progress or what-have-you; all you have to do is look at some of the drama bombs that are high-school relationships for proof.

Here is a third truth: there’s nothing wrong with having had your first relationship in your 20s, or losing your virginity at 23 — even if it was a casual encounter, rather than a committed relationship. These are just data points, not measurements of your worth or progress. They have no inherent meaning except what you give them. And the problem is that you’ve not only given them meaning, but you use that meaning like a scourge to whip yourself with. That’s going to actually make things harder, because you create a mindset that says “you should’ve been able to do this by now. You’re awful, you’re a loser, and now you have to make up for lost time.”

And that mindset is leading to the problems you’re having.

To start with, it sounds like part of the problem is that you seem to expect that each date you go on is going to lead to a relationship and, honestly, they aren’t. Dating is, to a certain extent, a number’s game. The early days of dating aren’t the start of a relationship, they’re about getting to know someone, seeing whether the two of you are right for one another and if there’s mutual interest and chemistry. A lot of times, there won’t be. Not because you did anything wrong or because you’re “defective”, just because you two didn’t mesh up the way you needed in order to work. As a wise man once said: you can commit no mistakes and still lose. That’s not weakness; that’s life.

But if you’re going into each date expecting this to be the last date you ever go on… well, that’s also going to be setting you up for heartbreak. You’re giving yourself unreasonable expectations, which makes disappointment almost inevitable. And if you’re expecting to go from “going on dates” to “a relationship” within a handful of dates… well, that’s going to throw people off. If that’s the vibe you’re giving, then it comes off as needy and desperate; that’s going to turn people off. And if it doesn’t… well, those are people you should run from so fast that you leave a human-shaped cloud behind you.

Worse, it sounds like you’re coming at this from a position of trying to fill a hole marked “girlfriend”, rather than coming to each person and wanting to get to know them. That too tends to put people off. It tells people that you’re less interested in them so much as what they represent, and that’s not a comfortable feeling.

Here’s what you need to do. First and foremost: you need to forgive yourself. You haven’t actually done anything wrong, but you seem to feel like you’ve f--k ed up somehow. So, ok, fine; forgive yourself for it. Forgive yourself for not living up to some bulls--t ideal. Forgive yourself for not being someone else. Grant yourself absolution for not meeting those arbitrary standards and then let them go. You now have a clean slate; you’re starting fresh and clean, to craft your life as you choose.

Next: stop going into dates looking for a relationship. Let go of the idea of relationships or trying to find one. Instead, you are going to treat each date as an opportunity to get to know somebody. Who are they, what makes them tick? What drives them, what do they live for, what do they value. And — more importantly — what makes them worth your time? What do they have going for them that makes them worth your interest? Why should you want to be with them? The fact that they’re attractive isn’t enough. The fact that they’re there is definitely not enough. You need to come to this from the position that you are the decider, that you are the catch and that they need to be deserving of you. Now this doesn’t mean that you look down on the people you date like a Roman emperor; you want them to be worth your time. You want them to be deserving of you. But your time is valuable and your heart is too precious to give to just anyone. So you will get to know people, go out with them on dates and see where things go.

Maybe they won’t be right for you as a romantic partner, but they could be good friends. Excellent! That’s a wonderful thing to discover. Others may be a great match as a sex-partner, but not compatible for a committed relationship. Again: excellent! Sex is awesome, and if that’s what you both want then hey, have a blast. But someone who’s worth having a relationship with will not be common; you don’t want to give your time or affection carelessly. So you give people a chance, but you keep your head and wait for someone who is right. You may find them quickly; you may not. That’s fine. While it may take you a little longer than you’d prefer, that’s OK because when you meet someone who is right for you, then it’s worth it.

The relationship isn’t the goal. The right person is. So focus on getting to know people and just enjoying yourself. When you meet someone who is right for you, then you’ll be ready. Not because they’re the person who said yes, but because they’re them, specifically.

Adopt this mindset, and you’ll not only have a better time, but you’ll meet a better quality of potential partner.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I have been in a relationship with my girlfriend for a little over 4 years now. Our relationship is one of those relationships where everyone considers our relationship the “perfect relationship”. My girlfriend and I fought pretty often about 2 years ago and we stopped, communicated, and decided that neither of us would like to leave our relationship because we were so in love.

Suddenly, we have began to argue again and honestly I didn’t even notice with my busy schedule and hectic life. Two nights ago, I noticed that she was acting very weird so I asked her what’s wrong and she told me that she noticed that we’re fighting again. I love her very deeply and I do not want to lose her. She told me that she loves me so much but she promised herself all of her life that she will not stay in a relationship that she is too comfortable with, and she wants to be genuinely happy. I feel that I have not been showing her the proper attention that she deserves and this is because I have been almost depressed lately because I lost my job and college overwhelms me.

When we were talking two nights ago she said that she didn’t know if she wanted to stay in this relationship because she was afraid that we would be wasting our time and only hurt ourselves more if we ever broke up because we tried once before to fix our relationship and here we are arguing again. We ended up agreeing to working on our relationship once more - mainly because I convinced her to try again.

What should we do?

Confused College Lesbian

DEAR CONFUSED COLLEGE LESBIAN: I hate to say it, CCL, but I suspect that you’re going to be having this conversation again in the near future.

A fact of the matter is: no matter how good your relationship is, you’re going to fight. Put two or more people together in a relationship and conflict will inevitably arise. It’s part and parcel of being individuals with their own wants, needs and concerns. Those will inevitably bump up against the other’s wants and needs and concerns and then boom: conflict. Never fighting doesn’t mean that your relationship is healthy; it’s entirely possible for a couple in a toxic relationship to never fight because one person rides roughshod over the other or someone has just learned to swallow their problems because their partner will just never address it.

It’s in how you fight that defines whether or not a relationship is in trouble. If your fights end with good-faith attempts to resolve the problem? That’s generally a good sign… as long as things actually get fixed, anyway. But if it just becomes a question of who is Less To Blame? That ain’t good.

Now, it’s possible that your relationship has come to its natural end. If you’re having the same fights over and over again, no matter how many times you’ve tried to resolve things then it may be that you’ve hit the point where you just aren’t right for each other any more. Which sucks, but it does happen; couples do sometimes outgrow their relationships and nobody is truly at fault. It sucks, but it does happen. It doesn’t mean that your relationship failed; it just means that your relationship has come to its organic conclusion.

But it’s the little things you bring up that make me suspect that the real problem is that your girlfriend wants out. Bringing up how she doesn’t want to stay in a relationship where she’s too comfortable, worrying that if you don’t break up now, it’ll hurt worse in the future… those are usually hallmarks of someone trying to find causus beli to justify a break-up. Some people feel like they need a “good enough” reason to end things and go looking for something that they can point to that says “this is why I had to end it.” And as much as I hate to say it, it kind of sounds like something your girlfriend is doing.

As painful as it may be, if and when she brings up the topic again, it may be time to call the question. You may just need to say “Do you want to break up?” and see where things go from there.

I hope I’m wrong, CCL. Hopefully things’ll smooth out as you get past the turbulence in your personal life and feel less overwhelmed by college.

But it may be something to bring up if your girlfriend brings this up again.

Good luck.

DEAR DR. NERDLOVE:  I am trying to find inner confidence that breaking up with my near 3 year relationship with my demisexual girlfriend. We have no sex life what so ever; maybe a bit of touching here and there but nothing major. I feel no commitment from her towards my family, and she has a view that we are going to be married in 4 years or less because that is when we finish college. I have lost many friends over her and lost my family’s trust more than once. I have committed to her and her family time and care and it feels like I can’t move forward with her. I have to call her all the time I can and if I do something wrong she will indirectly make me say sorry or feel bad. Any advice for me?

Time To Pull The Trigger?

DEAR TIME TO PULL THE TRIGGER: Occasionally I’ll get letters from folks who aren’t looking for advice; what they’re ACTUALLY looking for is permission to do what they’ve already decided. Sometimes it’s easier to ask a stranger to validate the choices you’ve already made than to just rip off that band-aid yourself.

Sounds to me like you know what needs to be done, TTPTT. All that’s left is just to do it. You sound pretty miserable and your relationship itself sounds like it’s gone toxic.

So the best thing you can do is do it quickly and cleanly. Just be firm: you’re breaking up with her, this relationship isn’t right for you and you don’t want to be in it any more. You don’t need to justify things or give any “reason” that’s “good enough” for a break-up. Wanting it to be over is the only reason you need. Phrasing it as anything other that “it’s over, I’m out” just means that it’s no longer a break-up, it’s the starting point of a negotiation. One that, unfortunately, won’t work out great for you.

So remember: It’s over, you’re not happy and you want out, goodbye, I wish you the best.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com