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Here’s the deal. I’m a professional and career-driven woman with all of the etiquette, style and hygiene that is needed for a professional woman. My boyfriend, whom I love dearly, is … not as polished as me. He does not have the same table manners or etiquette. Let me clarify — he is not a caveman! Rather, he is someone whose comfort level is not at a formal dinner, working your silverware from the outside in. He is a no-frills kind of guy and does not place value on artifice or even pay much attention to the fact he may not have stylish jeans, shoes or haircuts.  Instead he is the most genuine, authentic, kind-hearted, funny, communicative, thoughtful, loving, intelligent, supportive, affectionate, sensual, hopeless romantic I’ve ever met. I feel shallow that I care about how one holds their fork or rotates one of five pairs of shoes, even though it’s no consequence at the end of the day. I love this man and he has captured my heart. I just never saw myself with someone who maybe didn’t have all of the same etiquette and social manners as me. With that said, I have never felt more loved, able to communicate in a safe space, had more adventurous fun, felt more comfortable just being me, and we are oh so compatible in bed and the sex is holy moly! So, what the heck is up with me?! — Mainly Annoyed Nagging Nelly Explaining Regulation Silverware  Advertisement  Holy moly, indeed. So you are a professional lady with pressed pants and the fancy fork situation on lock. Your genuine, loving and supportive boyfriend, while not a neanderthal, could benefit from some Emily Post-style manners classes. But from your letter it doesn’t sound like a deal breaker, just a minor grievance. 

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If your specific concern is only in regards to business dinners and such, then by all means, teach him the rules. We don’t learn about oyster forks in school, after all. He might simply not know what’s up and would appreciate being let in on the big secrets of dishware placement. If it’s a sensitive issue for him, then blame a third-party target. “Honey, I love taking you to these dinners, but it would make things go smoother with my boss if we hold our cutlery as if we’re addressing the queen.” Et cetera.  Alternately, you could ask him to pay more attention to his appearance and manners as a favor to you on special occasions. Also, we’ve all been spending the majority of our time in our houses for the last three years-ish, so many of us don’t even know how to dress anymore. Show a little sympathy as he/we grow accustomed once more to wearing pants that chafe.  That said, some events have dress codes. It’s not so out of the ordinary to ask him to put away his cute house pants for an evening out. Compliment him before asking, using any of those descriptors you listed in your letter. And then give him specific advice. Some people’s notions of “dressing up” and “table manners” are wildly different from others. Like, if you want him to wear a tux or iron his socks, you’ll need to be specific in your request. Just don’t scold him publicly or use inflammatory language.  Approach moderations to his etiquette with courtesy and flattery, and it’ll be harder for him to take offense. “You look so hot when you wear pleated pants” is much nicer than being all, “I thought I told you to stop wearing Crocs in public.”  As to changing his day-to-day comfort levels and habits, that’s more of a long shot. If your dude is a no-frills, low-maintenance kind, then he’s probably not suddenly going to develop an affinity for Marc Jacobs and weekly beard oilings. You might take him shopping once in a while to give his wardrobe an upgrade for going-out events (and offer to foot the bill), and he might take your input seriously because we like to please our partners and look attractive for them.  But on the daily, who wants to give up their beloved sweatpants? Not I.  Advertisement San Mateo  What I was wondering was: How do you bring up the safe sex question with one-night stands? Because society harks about using condoms, but it’s really not sexy to bring out the hospital-grade sanitary gloves or ask about potential STIs when in the midst of ripping the clothes off a virtual stranger. So how do you ask them without offending or ruining the moment — Tired of Russian Roulette Sex  That is an excellent question. When it comes to safer sex with new people, the rules apply to everyone equally, whether it’s a one-night stand, a friend, an ex, or an ex’s ex’s friend.  It’s not an easy topic to bring up, however, especially if it’s someone you’ve just met because who wants to talk about gonorrhea when their lips look like pillows and all you want to do is take a nap on them with your face.  Most people advocate having The Talk early on. If this is a one-night stand you’ve prearranged, then I admire your organizational prowess, and you can bring up safer sex well before it all goes down. If it’s not preplanned, then bring it up before things get too sexy, preferably before clothes come off (shoes do not count). To paraphrase you, it’s harder to have a civilized conversation when one’s skinny jeans are around one’s knees. Also because lust is a notoriously unreliable life strategy. It clouds our judgment and can cause us to compromise our values in ways we wouldn’t otherwise.  While talking about safer sex is a good idea, it doesn’t have to be a Big Deal or a long-drawn-out thing with PowerPoint slides or 18-page documents. There’s also no need to use a terminal illness voice. You want to please this person, right? And you want them to please you? It’s much easier to accomplish this feat using words (“Mmm” does not count).  Most of the scripts I’ve come up with sound porny or cheesy, so you’ll probably have to improvise, but here are a few potentials anyway:  The sex boundaries angle. “Is there anything you don’t like/I should avoid?” And then after they tell you, you can talk about your own boundaries. If that includes using condoms or gloves with new partners, then say so. This addresses safer sex concerns AND helps you learn how to please each other better. Win-win.  The flattery angle. “I’m so stoked to be seeing you naked! That’s why it’s important to me to keep my sex partners healthy and hot. Let’s talk for a few minutes about statuses and the last time we were tested, and for what.”  The direct, pragmatic angle. “Before we get too far, let’s talk about protection ...”  The kinky angle. I can think of three scenarios off the top of my head to incorporate gloves in a fun, role-playing way. This doesn’t exactly get you off the hook from having The Talk, but if they’re into role playing, and you want to be safe in a creative way, it could work.  When planning, it’s helpful to have sex stuff like barriers, lubes, etc. handy (on the nightstand, in your bag) so that you don’t have to stop and trek to the bathroom down the hall — or stop entirely, if neither of you is prepared! Also helpful to remember is that no matter how awkward such a conversation may be in the moment, it’s far preferable to the one that goes, “So … I found this weird bump.” It’s your health and well-being, remember. Don’t feel like you should compromise that because “dental dam” is such an unsexy word. (Ideas for rebranding it? Beave sheet? Clam dam?)  As with most things, you’ll get better having this conversation the more you do it. And if any of your partners balk at having a safer sex conversation, or brush off your concerns, that is a pretty good litmus test about whether you want said person anywhere near your nether bits.  Good luck, TORRS. I wish you all the sex!  (Anna Pulley is a syndicated Tribune Content Agency columnist answering reader questions about love, sex and dating. Send your questions via email (anonymity guaranteed) to redeyedating@gmail.com, sign up for her infrequent (yet amazing) newsletter or check out her books!)