Dear Miss Information,

My best friend recently got back together with her boyfriend. They didn't use condoms while they were together — she was on the Pill — and they're not using condoms at present. She said he only slept with "a few people" while they were broken up and that he used protection. I told her I think that's crazy. She should make him get tested and get tested herself. But is it too late? If he has anything she's probably been exposed to it already. She doesn't wanted to get tested because she doesn't have insurance and is afraid of needles. I also think deep down she's either in denial or doesn't think it's necessary. Do you have any advice? I want her to see how serious this is.

P.S. Did I mention her boyfriend's a scumbag? — Unhealthy Friendship

Dear Unhealthy Friendship,

Hooray for you for taking to heart (and vagina) all those pamphlets they handed out in health class, and for wanting to look out for your friend. I have that nurturing instinct as well, though less kind synonyms might include "intrusive," "caretaker," or "adult child of an alcoholic."

You can have opinions about your best friend's conduct, and express those opinions, but you cannot control it. Which feels pretty terrible — it's like watching a friend who's about to drink and drive. At least with the booze cruiser you can grab their keys or offer them a ride, but it's less socially acceptable to come bursting into the bedroom, confiscate the suspicious package, and offer the use of your Rabbit as an alternative.

This is about gentle but persistent persuasion. It doesn't take an overpaid branding consultant to know that "Your boyfriend's a dick!" isn't a winning campaign message. Giving her the information she needs to get tested and making it seem as efortless as possible are better tactics. Do you have that information, Unhealthy? Do you know that most STD tests nowadays don't involve needles? Although blood tests are still the gold standard, you can get tested for HIV using your saliva or a quick finger prick. Insurance doesn't have to be an issue, either. Enter "free STD testing + [your county]" into Google, find your local Planned Parenthood, or buy an at-home testing kit. It's not free, but it's cheaper than paying for a full-on doctor's visit.

Once you have all the information, compile it into a nice little email or go old school and make some print-outs. Give it to her, along with an offer to go get tested alongside her (not necessary, I'm sure, as you are probably the type who smears on spermicidal lip balm before a French kiss). After that, all that's left to do is STFU and get on with your life and your friendship. You might also want to see what you can do about making peace with the scumbag (I know the type, 'cause I've dated him). The hyperactive worrying might stop if you get to like him better and trust him. If that doesn't work, there's nothing wrong with keeping your enemy close. You may get the ammo you need to convince your friend to find someone better. Then she'll start going bareback with him, and you'll have a whole new set of worries. Isn't codependency grand?

Dear Miss Information,

I recently dumped my horrible (alcoholic, mean, unwashed, bad-in-bed) boyfriend of four years and started dating a man I think is absolutely incredible. He's smart, sexy, kind, funny, well-mannered, and he really, really likes me. My only problem? I don't feel like I deserve him. I stayed in a bad relationship for a long time because I didn't believe anyone worthwhile could ever love me. I understand this. I also understand that it's totally irrational: I'm reasonably smart and attractive, and I've never really been short of people who wanted to date me. I'm afraid that I'm going to sabotage this new, good relationship with jealousy and insecurity and pessimism because of my ridiculously low self-esteem. I really don't want to do this. I lusted after this new man for years — we even briefly got together once before, until I threw it away because I was so convinced he was out of my league. I want this to work. Please give me some ideas about how I can not fuck it up this time around. — Scared Shitless

Dear Scared Shitless,

Therapy? Sorry if that's redundant, since your letter makes it sound like you're already in therapy. Or maybe you just own a lot of self-help books.

No one wants to make the same mistake twice. The bummer is that most of us will. It's difficult to change the way you're hard-wired. The key is knowing you're making the mistake, then taking steps to stop making the mistake, minimize its damage, and/or reverse it. Those who get really good at that can move on to the next level, which is knowing when you're about to fuck up, understanding the reasons why, and removing the potential triggers. The final stage involves looking down on everyone, using words like "spiritscape" and "personal journey," and composting your cat shit. In other words, there's no such thing as a mistake-free, non-fucking-up person, and anyone who think they are one is probably not someone your new man would want to be with.

You talk about jealousy, insecurity, and pessimism. How do these play out in your day-to-day as a couple? Are you pissy when he goes out without you? Do you grab his cell phone or demand to know who's on the other end when he gets a text? Is it a big issue if he compliments another female, even though you're always going on about Idris Elba and that one shirtless picture? If he could critique you, free of fallout, what would be his five biggest issues with the way you act in the relationship? Do you know what you need to do to work on them? If not, ask him... though maybe not all at once. You could solicit feedback as it's happening. The next time a recurring battle revs up, ask what he thinks you could do to avoid a repeat.

I also want you to think about how many real, concrete indications you've gotten from him that you're messing up and how much of it is in your head. I had an old therapist that had me write out a list of all the things I thought people were saying about me and then put checkmarks next to the ones that had actually been said. If you can get over the sudden realization that you're a paranoid, tin-foil-hat-wearing narcissist, the disparity can be pretty reassuring.

Finally, ask yourself if "I don't deserve him" is code for "I'm not really in love with him." I don't want to advocate for a breakup or shit on anyone's romance, but sometimes we convince ourselves that we have bad taste or don't deserve good things when the reality is we're with the wrong person. This is so (so) common for people who've been in abusive relationships. You've been mistreated for so long you feel like you're contractually obligated to stay with the next nice person. If that's the case, move on. I promise you there're more where he came from.