Q: How do you handle it if your partner constantly apologizes during sex? “Sorry, sorry, sorry…”
With sensitivity, tact, and compassion—and if none of that shit works, try duct tape.
Q: Should I continue to have casual sex with someone I’m in love with?
If it’s casual for them and not casual for you, and they’ve made it clear it will never be anything other than casual for them, you’re going to get hurt—which I suspect you know. Now, if you think the pain of going without sex with them will be greater than the pain you’ll feel when they inevitably meet someone else and move on, by all means keep fucking them. (Spoiler: the pain of the latter > the pain of the former.)
Q: Best tricks for a quick female orgasm & how to keep yourself from overthinking it?
My female friends swear by a little legal weed, where available (or a little illegal weed, where necessary), and a nice, big, powerful vibrator.
Q: My five-year relationship ended abruptly. Is there a time frame for getting over it?
Studies vary. Some have found it takes the average person 11 weeks, some have found it takes half the length of the relationship itself, some have found it takes longer if it was a marriage that ended. But don’t wait until you’re completely over it to get out there — because getting out there can help you get over it.
Q: Besides a fiber-rich diet, what are your tips for a newbie to anal play? Size is a BIG factor and it’s creating a HUGE mental block whenever anything goes near my hole.
Start small, e.g., lubed-up fingers and small toys. And don’t graduate from tongues/fingers/toys to someone’s big ol’ dick in a single session. Start small and stay small until your hole’s dread at the thought of taking something HUGE is replaced by a sincerely held, quasi-religious belief in the absolute necessity of taking something huge.
Q: What is the formula for getting comfortable farting in front of a partner?
Same as comedy: tragedy + time.
Q: In the era of online dating, how do you navigate the people who think the grass will always be greener and have difficulty committing to truly building a relationship?
The expression “the grass is always greener on the other side of the fence” has its roots in a Latin proverb first translated into English in 1545 — which means the sentiment predates dating apps by, oh, roughly half a millennium. But the “paradox of choice,” or the idea that people have a hard time choosing when presented with too many options, has certainly complicated modern dating. But too many options beats too few, in my opinion, and it certainly beats no options at all, e.g., deserted islands, compulsory heterosexuality, unhappy arranged marriages, etc.
Q: Any advice for a 22-year-old woman who meets only sad boys who need a mom?
Your handwriting is such that I thought you wrote “sub boys,” and I was going to respond, “Enjoy.” But then I reread your question: sad boys, not sub boys. Okay, if you’re meeting only one type of person or all the people you’re meeting have a certain character flaw, either you’re seeking that type of person out — consciously or subconsciously — or you’re projecting your own shit onto that person. This is a case where the best people to ask for a gut/reality check are your actual friends, not your friendly sex-advice columnist.
Q: Will you be my sperm donor?
Well, that depends. Are you male, between the ages of 25 and 55, and (my entirely subjective notion about what is) hot? Then sure!
