Question 1

Is it normal to not orgasm during sex?

Accepted Answer

Yes — it's one of the most common questions Deni ever received, and it never stopped surprising her how many women thought they were the only ones. Many women simply don't orgasm from penetration alone; the anatomy doesn't work that way for most bodies, and that's not a flaw waiting to be fixed. Deni's answers on this always started with taking the shame out of the question before ever getting to technique. Dear Deni: Orgasm and Female Pleasure covers this in depth.

Question 2

How do I talk to my partner about a fantasy I'm embarrassed about?

Accepted Answer

Start small, and start with curiosity rather than a confession. Deni always said framing a fantasy as "something I've been wondering about" lands very differently than framing it as a secret you're finally admitting to. Timing matters too: a calm, private moment works far better than bringing it up mid-argument or mid-sex. Deni's letters on this exact topic, including several from people terrified their partner would react badly, are collected in Dear Deni: Fantasies and Group Sex.

Question 3

Does penis size actually matter?

Accepted Answer

Less than most people think, and in different ways than most people assume. Deni answered this question more than almost any other topic that came through her inbox. What she found, again and again, was that confidence and technique mattered more to partners than the number itself, and that most of the anxiety around size lived entirely in the asker's head rather than in their partner's actual experience. She never dismissed the worry, though — she just answered it honestly. See Dear Deni: Oral Sex and Size Matters for her full, direct take.

Question 4

How do I bring up wanting a threesome without scaring my partner?

Accepted Answer

Timing and framing matter more than the request itself, according to Deni — bringing it up as a genuine, low-pressure conversation rather than an ultimatum changes everything about how it lands. She also encouraged people to get clear on their own "why" before the conversation, since partners can usually tell the difference between curiosity and dissatisfaction being disguised as curiosity. Deni's real letters on this, including a few from people who got it wrong the first time and tried again, are in Dear Deni: Fantasies and Group Sex.

Question 5

Why did the spark disappear in my long-term relationship?

Accepted Answer

It's rarely one big reason — usually it's a slow drift neither partner noticed happening, built from small missed moments rather than one dramatic event. Deni often pointed out that couples stop reaching for each other long before they stop loving each other, and that the two aren't the same thing at all. Dear Deni: Intimacy and Relationships addresses this directly, through letters from couples married, dating, and everywhere in between.

Question 6

How do I flirt without seeming desperate or awkward?

Accepted Answer

Confidence reads less in what you actually say and more in how relaxed you are saying it — Deni's advice consistently came back to that point, no matter how the question was phrased. She was also quick to remind people that a slightly awkward, genuine moment usually lands better than a polished line that feels rehearsed. Dear Deni: Flirting and Dating is full of her real answers to people convinced they'd already blown it.

Question 7

Is it normal to be attracted to women even if I've only dated men?

Accepted Answer

Completely normal, and far more common than most people realize — attraction doesn't always show up on a predictable timeline, and Deni made a point of never rushing anyone toward a label they weren't ready for. She treated every one of these letters with the same patience: listen first, and let the person figure out what it meant for themselves. Dear Deni: Lesbians and Bisexuals was built entirely around letters like this one.

Question 8

What's the best way to last longer during sex?

Accepted Answer

Technique matters less than most guides suggest — communication and pacing matter more, according to Deni, who often redirected this question toward what was actually happening between two people rather than a mechanical fix. She covered specific techniques too, but always framed them as tools within a bigger conversation, not a standalone solution. It's covered in full in Dear Deni: Sex Positions and Techniques.

Question 9

How do I tell my partner I'm not enjoying oral sex the way they're doing it?

Accepted Answer

Directly, kindly, and without waiting for them to guess — Deni was firm on this point, because she'd seen how much resentment built up in people who stayed quiet for years hoping their partner would just figure it out. She encouraged specific, gentle guidance in the moment rather than a big after-the-fact conversation. Deni's full approach to this is in Dear Deni: Oral Sex and Size Matters.

Question 10

Can wanting a threesome mean something is wrong with my relationship?

Accepted Answer

No — curiosity and dissatisfaction aren't the same thing, though Deni acknowledged they can feel identical from the inside, which is exactly what made so many people afraid to even ask the question. She encouraged readers to get honest with themselves about which one they were actually feeling before bringing it to a partner. Dear Deni: Fantasies and Group Sex unpacks that difference across several real letters.

Question 11

Is it too late to fix intimacy after years of it fading?

Accepted Answer

Deni never believed in "too late" — only in whether both people were actually willing to try again, which she considered a far more honest question than how much time had already passed. Several of her letters came from couples decades into a relationship who assumed they'd missed their window, and her answer was consistently the same: it's never too late if you're both still asking the question. Dear Deni: Intimacy and Relationships has several letters exactly like this.

Question 12

How do I know if I'm bisexual or just curious?

Accepted Answer

There's no test and no deadline — Deni's answer was always to let the question sit rather than rush toward a label, since she believed certainty wasn't a requirement for exploring attraction honestly. She was especially gentle with people who felt pressure to have an answer ready before they'd even had the chance to explore the feeling. Dear Deni: Lesbians and Bisexuals explores this at length, through letters from people at every stage of that process.

Question 13

What sex position is actually the best?

Accepted Answer

There isn't one — the "best" position is specific to the two people in it, not a universal answer, and Deni was refreshingly blunt about how much of the advice out there ignored that basic fact. She preferred to talk through what someone was actually trying to achieve — depth, closeness, control, comfort — and work backward from there. Dear Deni: Sex Positions and Techniques explains her reasoning in full.

Question 14

How do I make the first move without ruining a friendship?

Accepted Answer

Carefully, honestly, and prepared for either answer — Deni never pretended there was a way to remove all the risk, only ways to handle it with more grace. She often pointed out that the fear of ruining a friendship usually says more about how much someone values the other person than about the actual odds of it happening. Dear Deni: Flirting and Dating has real letters from people who took that exact risk, some successfully and some not.

Question 15

Who was Deni, really?

Accepted Answer

A real woman who ran an advice column for five years before passing away suddenly, leaving behind an archive of real letters from real people who trusted her with the questions they couldn't ask anyone else. She had no formal credentials — just lived experience, and a way of answering that never once talked down to the person asking. Her full story, and her complete real letters, are collected in Dear Deni: The Complete Collection.

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