Hello, Internet! Welcome to Ask Dr. NerdLove, the only dating advice column run by the Herald of Andraste, Inquisitor of Romance.

This week's question is the Inception of dating questions. At its surface, it's a question of setting boundaries: how do you get your partner to stop behavior that's hurting you? But the question has layers that mask the core problem.

Take a deep breath and grab your totem, because it's time to go deeper.

Let's do this.

Doc,

I've been dating this woman for three months. I'm 26, she's 20.

She's really a very good person, in most respects — except that she doesn't respect relationship boundaries. She spends a lot of time with a guy she used to sleep with—one of her best friends—who admitted to having feelings for her after we started dating, and recently has been texting a man from high school who has openly asked her to stay the night as his place, though she hasn't spent any time with him as far as I know.

I have communicated how uncomfortable I am with both of these relationships, though I would never go as far as to ask her to drop them because I don't want to be controlling. Besides that, our relationship is fairly fresh, and she has said explicitly that if I asked her to choose between me and the best friend, she would choose him.

I suffer from anxiety, and have been in relationships where I have been cheated on repeatedly. I try not to bring my past into new relationships, but that fear is always there and this behaviour does not help to ease my mind whatsoever.

A female friend of mine who knows her very well told me that she believes that she is just beginning to realize her worth as the result of our relationship, as I am the first man she's been with who doesn't just use her for sex. She also suspects that my girlfriend is going through some sort of rite of passage for a woman in becoming secure with herself, which supposedly has her addicted to the "good" feelings that come from the attention of men.

I don't know what to do. We have a good relationship, although it has been strained by this and some medical issues in her life recently that have reduced our intimacy to zero over the last few weeks. I care about her immensely and don't want to walk away yet, but I also don't want to keep feeling this way. It keeps me up at night.

Any thoughts on this matter, and what I can do to save the relationship or myself are appreciated.

Sincerely,

Up All Night

As with many of the people who write in, UAN, you have a problem, but it's not quite the problem you think it is. There are a lot of layers to this problem and we're going to need to get to the core to fix things.

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Now, fair warning: this is rarely pleasant. It's going to be more than a little painful. But it is necessary.

Let's start from the outside and work our way in.

The external issue is that your girlfriend of three months is in contact with people who make you uncomfortable - an ex-lover and a former classmate - because you believe they have designs on her. Fair enough; that can be uncomfortable, especially with your background. There's that selfish part of you that wants to say "please stop talking to them" (between you, me, and the readers, that's what you really want) but you're respectfully refraining from actually doing so because that'd be controlling.

And so the surface question is "what do I do about this?"

You know you don't really have a play here. She's already told you where you stand in her priorities: she values her ex more than you. As hard as it can be, you don't want to take this personally. This isn't a comment about how she feels about you as a person, just the circumstances of your relationship: he's her best friend with years of history and you've only been her boyfriend for three months. Honestly, if your theoretical girlfriend or boyfriend was willing to throw over their BFF for you after only three months, that would be a giant warning sign that somebody has over-invested in the relationship.

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On the surface - and what I would normally suggest - is to use your words. But they have to be the right words. It's great that you've tried to establish some boundaries, but you have to set up the right ones and in the right way.

See, I think you made a mistake by framing it as "your relationship with these people makes me uncomfortable". You may not have intended it that way, but that sounds less like "Hey, I'm insecure at times" and more like you're saying "I'm not telling you drop them, buuuuut…." That's some passive-aggressive controlling bullshit right there; it communicates that you know if you explicitly tell her to choose, she won't choose you so you're trying to backdoor your way there instead.

What you'd want to do is make this about how you feel and how she can help you feel better. The surface problem isn't with her behavior in this case but how you feel about it. So what you need is less that she stops being friends with this guy and more that she helps you walk back from the edge when your anxiety starts to raise its ugly head. Don't tell her what she can't or shouldn't do, ask her to provide you with a little reminder that she's chosen to be with you and is happy with you.

You want to tell her "Hey listen; my relationship history has left me a little insecure and I feel a little threatened by your relationship with your friends. Sometimes I get a little anxious about it; it has nothing to do with you and everything to do with me. I'd appreciate it if on occasion you could provide me with a little reassurance when my anxieties get the best of me."

But that's the surface issue - not the real problem. For that we have to dig in a little further.

At the next level, we're getting closer to the core of the issue - you know that your relationship is currently on shaky ground. Your level of intimacy has dropped to zero, which is a bad sign. It's one thing if the sex has slowed down; those unnamed medical issues could make sex undesirable, uncomfortable or even impossible. But it's the way you phrased things - that your intimacy has gone to zero, that sets off my Spidey-sense. If she's withdrawn all intimacy - down to anything more than occasional kisses or cuddling on the couch - that's usually a sign that she's withdrawing entirely. It's no wonder that you're feeling anxious right now - you're feeling like she's getting ready to ditch you. At this level, what you're asking is, "can I trust my girlfriend," and you're not liking the answer you're getting back.

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But that's still not the right question. For that we have to go down to the core.

Because the question isn't how to establish those boundaries or whether you can trust her, it's whether you should be dating her at all.

One of the most important aspects in a relationship is that you need to be compatible with one another; not just sexually, but in lifestyle, values and maturity levels. And right now… you're just not there. She may be what you want, but she's definitely not what you need. With your past and your issues, you need someone who's in a different place in their lives - someone who's (emotionally) mature and established. And I hate to say it, but that's not your girlfriend.

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Let's look at the facts here: she's 20, you're 26. That's only six years' difference… but those are some critical years. You pack a lot of living in those six years. You see the world entirely differently. You're relatively established in your life, while she's still very much in the formative college years, trying to figure out who she is. Her priorities in life are going to be pretty damn different from yours in general. And that includes how she feels about relationships.

I think that your friend is right: your girlfriend is starting a new stage in her life. She's starting to feel more confident and more secure, like she has more value as a person. In a lot of ways, it feels like she's just shed her old life and she's stepped blinking into the light of the new one. She's getting a lot of new attention and that can be fairly intoxicating… and it can be hard to not respond to that attention. She may be realizing that she has more options than she thought she did, and is getting high off the new possibilities. Change like that often means letting go of parts of your old life, and that means relationships, too.

This doesn't mean that she's a bad person. This doesn't mean that you're a bad person. It certainly doesn't mean that she doesn't genuinely care for you. It just means that she's not in a place where this kind of relationship can work.

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And to be honest: I'm not entirely sure you're there either - definitely not with her, anyway. You've still got some wounds from being mistreated in past relationships and I don't think they've healed up all the way yet. Anxiety and insecurity are relationship-killers, whether they're directed inwards or outwards. It makes it impossible to relax and to trust in your partner, in your relationship and in yourself. You can't be with someone, really with them when you're constantly waiting for the Sword of Damocles to fall.

Y'know. Like you are right now.

I realize this isn't what you were hoping for. You were hoping for help, not for me to tell you that I think your relationship is going to end sooner rather than later. And I realize it's going to hurt.

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But that pain? You can use it. It can either be the pain that cripples you, or the necessary pain that comes with healing. Setting a bone hurts. But when the pain fades, you realize how much better you feel.

It may not be a bad idea to take a little break from dating while you take some time to work on your anxiety issues and learn to trust again. Because once you've started dealing with those core issues - the fear and anxiety that you've been dealing with? You're going to find that you'll be a new man, better, stronger and braver than before.

It'll be hard.

It'll be painful.

But it'll be worth it.

Good luck.

Have you dealt with a break-up only to come back better than before? Share your thoughts and experiences in the comments and we'll be back in two weeks with more of your dating questions.

Ask Dr. Nerdlove is Kotaku's bi-weekly dating column, hosted by the one and only Harris O'Malley, AKA Dr. Nerdlove. Got a question you'd like answered? Write doc@doctornerdlove.com and put "Kotaku" in the subject line.

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Harris O'Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr. NerdLove and the Dr. NerdLove podcast. His new book Simplified Dating is available exclusively through Amazon. He is also a regular guest at One Of Us. He can be found dispensing snark and advice on Facebook and on Twitter at @DrNerdLove.

Illustration by Tara Jacoby