Miss Information: My boyfriend went back to his ex, then came back to me. How can I ever trust him again?

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My boyfriend went back to his ex, then came back to me. How can I ever trust him again?

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Dear Miss Information,

I am dating a wonderful man. We had a rocky start. The first few months we started seeing each other, he was still very emotionally attached to his ex-wife. I knew it was silly to get involved with him while he wasn't completely over her, but the heart and the groin are not always good at taking directions. Anyway, he broke up with me after a few months in an attempt to get back with his ex-wife when he heard that she was planning on getting re-married. The breakup lasted about a month. He seemed to immediately regret it. At the time, we worked together, and I saw him slowly register that what we had was fantastic and that their problems still existed. The ex-wife, in the meantime, dropped her fiancé, and they got back together. Within a week of breaking up with me, he started telling mutual friends that he felt that he made a huge mistake but now felt stuck. To say I was heartbroken is a complete understatement. He ended up breaking things off with her and finally moving the rest of his belongings out of their shared storage shed and completely cutting off all communication. He came back to me, and after hours and hours of talking to make it work, we made it work.

It has been a year. He has been amazingly loving, devoted, open, and all of the other things he was not when he was still attached to his ex-wife. I should be happy, but I am still so cripplingly insecure. I am jealous around other women, I fear extremely ridiculous and implausible scenarios (like, fearing that he has prostitutes over to his house when his roommate is away — really crazy shit) and I just cannot trust him. He didn't cheat on me with the ex, but it felt that way. How do I get over the jealousy and insecurity? I am gunning for some concrete solutions, not just "love yourself" or "have a talk with him." We've talked to death. I am normally quite confident, but this relationship knocked me over. I want to be with him and he wants to be with me. Can you give me a mantra or something to get over this jealousy and insecurity? It is making us both miserable.

— Lost Baggage

Dear Lost Baggage,

You don't want me to tell you to "love yourself?" Oh man, I'd like to think I'm better than that. Besides, I don't think you need much help in that department: you seem pretty grounded, and your sense of self seems fine. I guess I'll have to save "braid flowers into your hair and commune with the Moon Goddess" for someone else.

Though a year is a long time to live with this "crazy shit," the lack of trust you feel is completely understandable. Still having trouble owning your discomfort? Here's what I see going on.

1. Your boyfriend did act hurtfully — he just didn't "cheat," meaning that he filed all the necessary paperwork before he got back with his ex. Of course, that notary stamp doesn't make the breach of trust any less painful for you.

2. When you first started dating, your boyfriend was clearly an emotional mess. Which is fine; he's human, it happens. However — and let's bold this — just because someone is in a really bad emotional/mental place, doesn't mean their actions somehow "don't count." He can't write off his hurtful behavior as being a consequence of his pain. Now you're stuck trying to reconcile the sins of the "wounded" boyfriend who hurt you against the "wonderful" boyfriend you're with now. They both inhabit the same body.

So, Lost Baggage, what to do? Have you considered loving yourself? Talking it out? (Ho ho ho, I'm hilarious.) Start by re-framing this issue. It's not you irrationally being upset about this thing that happened forever ago. It's a legitimate trauma that your relationship survived, and will take both of you to work through. So let the self-criticism go; though your thoughts are crazy and aggravating, directing annoyance inward isn't helpful. Let's channel that rage into something more constructive.

First, think in concrete, brass-tack terms. What are your biggest sore spots? Work to confront these things head-on, rather than shrinking from them and licking your wounds. If you're feeling jealous of a hot girl he's talking to, for instance, get him to introduce you: nine times out of ten, another woman becomes less threatening if you get to know her. If his roommate is going out of town, don't give the hookers enough time to get in the hot tub: propose a date night, or have him cook dinner for you to prove no one's hiding in the closets. Work on demystifying whatever you're afraid of, and you'll find that your fears shrink. It will likely feel clunky and awkward at first, even just admitting the depth of these insecurities. It's going to take both of you to dig out of this trust-foxhole.

If he truly is as supportive and blameless as you say, and your thoughts are the biggest barrier to your happiness, there are healthy ways to reclaim your own mind. It could be something that takes your mind off of your relationship and gives you a new skill, like taking an art class. It could be trying to retrain your negative thoughts through something like meditation or yoga. It could be therapy, either by yourself or as a couple. Anything that pulls you out of your current mental framework would likely do wonders for you.

Along these lines, devote some real thought to what, specifically, is bugging you. Did his cheating-non-cheating trigger something bigger in you? It's pretty amazing how painful experiences have a tendency to link up and form meta-painful experiences that grow multiple heads and hijack your thoughts. If you're battling not just this recent episode, but rather an insecurity Hydra, you should figure that out and arm yourself accordingly.

I wish I had easier tips for you, like "Try holding hands and crying," or "Get one of those monkey-backpack leashes that lame people put on their toddlers," but I don't. It's going to take some pretty intensive work on both of your parts: he'll need to own his hurtful behavior and be aware that triggers may still exist, and you'll need to work to punch holes in your fears. I wish you luck. And if these solutions still don't seem concrete enough, have you considered trust falls? A ropes course? I'm happy to refer you to my sixth-grade gym coach if you have further questions.

Dear Miss Info,

I'm a nineteen-year-old college freshman, and lately I've been fixated on a guy I had a mini "fling" with —  meaning a hot and steamy makeout session. He's the guy all the girls say they'd shag if they had a chance, and although I was interested, I didn't think he'd ever flash a look my way. He hit on me pretty hard, and we ended up making out in his bed. Constant invitations to parties continued and I ignored them, thinking I was a one-night fling and he'd never come back for more. I was wrong; he persisted, and it worked. I finally gave in, and boom, steamy and passionate make-out session number two ensued.

College is a time where young adults have their most pleasant sexual experiences, but I wanted this one to seem real and turn into true love. How girly of me. I'm beginning to think that all I am is a makeout buddy and nothing more. How can I handle this? And how do I keep myself from falling for a boy's silly line ever again?

New to This

Dear New to This,

Oh, it's soapbox time! First: "How girly of you" to want a real connection with another human being? Okay, yes: for some reason honest emotional sharing has gotten cast as the realm of the female, and my feminist/egalitarian heart breaks. Because in that context, "girly" is synonymous with "naïve" or "silly," when really, that desire is a fundamental human trait. And to call the yearning for a deep relationship "girly" is also unfair to men, many of whom want just the same thing, but are conditioned to feel that voicing those impulses is, well, girly. I'm not coming down on you, New to This, I'm coming down on all of us. Can we let go of this shared sense of girls clawing for intimacy and boys pounding beers to numb the feelings? It's not doing any of us any favors.

But okay, to your question. Are you concerned about being used? It seems like you're the one setting up roadblocks here, not him. If you think you're falling into too-casual territory, ask him about it. Keep it as coy banter: "Hey, are you going to take me out properly one of these nights?" If he sputters or gets noncommital, move on. If he's excited and into it, then skip off into the sunset. Again, remember: boys are emotional beings too, no matter how sparkling their eyes or high their cheekbones.

You're right to be cynical, though, and good for you for keeping your bullshit-detector sharp. Just don't take that cynicism so far that it hardens into a shell around you. This dude may be a worthy contender, or he may not — but you won't find out until you give him a chance either to prove himself or to fall flat.

P.S.: "College is a time where young adults have their most pleasant sexual experiences"? I'm sorry, I seem to have just choked on my sixth beer. Which I am drinking specifically to drown out the memories of my college sexual experiences. Don't put too much weight on sex, sister. Skip class, say pretentious things you'll come to regret, and make awesome friends. The rest will fall into place.