Miss Information

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I'm going on a trip with an old flame, and my boyfriend's freaking out.

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Dear Miss Information,

I've been with my current boyfriend for around eight months. He knows I have quite a history. A few days before I got together with him, I slept with one of my close guy friends who later admitted to having feelings for me. This summer, I'm going traveling with a group of friends, including that guy friend but not including my boyfriend.

Although I booked this trip way before we started dating, I do feel guilty, and my current boyfriend is uncomfortable with the situation. He's gone from being incredibly laid back to dictating what I wear and how I behave while on vacation. He claims to trust me, but, obviously, I doubt this.

I'm beginning to get frustrated, and even though the rest of the relationship should be great, it isn't. We're constantly fighting over this issue and others that stem from it. I'm also now worried he'll go out of his way to spite me while I'm away. I don't know how to deal with this. Should I continue this relationship? And if so, how can I make him feel more comfortable?

— Soon to Snap

Dear Soon to Snap,

It sounds like there's a serious Cold War going on between you two, and a house divided against itself cannot stand. (These metaphors aren't going to mix themselves, people.) First, let's clear up a few things. He's dictating what you wear and how you behave? You think he's going to do something to "spite" you while you're away? If these things are actually going on, shut it down. This crosses the line from "insecure boyfriend" to "desperate and controlling." You've been dating a relatively short time. Is it possible that this trip is just the first catalyst to bring out some ugly truths about his personality?

Of course, a letter is a two-dimensional format. I'll give him the benefit of the doubt. Let's say there's nothing insidious about his nervousness; let's say his reactions as you reported them are some combination of his insecurity and your fears about his insecurity. If this is the case, sit him down for a tough-but-compassionate talk on acceptable boundaries. "I will email or call every other day, wi-fi permitting" is a reasonable agreement; "I will wear a muumuu covered in a parka" is not.

He needs to know that he can't keep you in a jar. Just as importantly, you need to trust that he will not do anything hurtful while you are gone. If you can't both come to this neutral place, you'll have to ask yourself: why fight to keep someone whom you suspect wants to undermine you?

Dear Miss Information,

I'm twenty-five years old and I have some social/relationship "problems." First off, I am bipolar. Next, I never went to public school. I was home-schooled all my life, and that has greatly affected my experience in and confidence about social interactions. I'm overweight, which is partly genes and partly meds for bipolar disorder. I don't exactly have Brad Pitt looks, or Brad Pitt anything. A girl I was trying to hook up with over the internet once told me I wasn't physically attractive. That didn't help things.

I don't drink or smoke, and clubs just aren't my thing. I'm just at a point of life where I realize I should already have or had a girlfriend/been married. I should be somewhere completely different. It's depressing when I see couples holding hands, hugging, kissing, etc., because I want that, but I know that the chances are becoming slimmer.

When I meet a girl I like, I'm careful about how I say things or do things. I may manage to get a phone number and text for a while, but nothing comes of it. I was raised in the kind of home where I just never was introduced to the whole "girlfriend" thing.

I don't know why I'm still typing, but I'm just really scared that my destiny at this point is to be alone. I can't live that way. It's part of human nature to desire companionship. But my lack of experience and confidence have taken their toll on me. Is there anything that you believe would help?

— Depressingly Lonely

Dear Depressingly Lonely,

A solid portion of emails I get are from people just like you — some men, some women. Each of them is convinced they're at a unique disadvantage, and each of them has resigned themselves to a life of cat ownership and scrapbooking. Here's the thing, though: you can't all be doomed. In fact, I believe none of you are. Maybe the first step in climbing out of your hole is to realize that not everyone has the perfect, socially-adjusted, easy time you think they do. Everyone's got shit. It's a matter of finding people whose shit corresponds to yours.

You have a lot going on, but none of it is insurmountable. What's going on with your bipolar disorder? Are you in a relatively stable place and getting the support you need? If not, shelve everything until you feel "together." Your own equilibrium is a necessary foundation for any future relationship.

As far as your other problems, none are the kiss of death. Plenty of charismatic people were homeschooled, and drinking and smoking aren't requisites for a fulfilling social life. Obviously, it sucks to be told you're not attractive. But that's one girl's opinion. I went to a liberal-arts school; I can personally attest that non-conventionally-attractive people get laid all the time. The key is to stop "trying to hook up," and start "trying to make connections." The former is desperate and off-putting. The latter is a necessary part of being human.

The more you focus on what you're not getting, the more you squeeze the life out of it. (Your goals are like the bunnies from Of Mice and Men. Careful with them!) To loosen your grip a bit, set reasonable expectations for yourself. "Be married by now" is not a reasonable goal. "Go to the gym" or "try one new thing each week" is. Let go of the panic voice as much as possible, and focus on building stairs out of your isolation.

In short, DL, there are more lonely hearts out there than you might think. You're in good company. This should encourage you (and everyone else in your position): you're not "behind," you're not "broken," and you're not doomed to anything. Find a therapist, take a class, get a goldfish. Plug into the world around you. As long as you don't lose yourself to self-pity, you'll be fine.