Dear Dolly

1. Asking for Help is a Healing Act.

What I learnt from sharing my most private pain with a semi-professional problem-solver was that the mere act of asking for help was, in itself, healing.

The power of articulation. The author's personal experience, including writing to Nick Cave during a difficult time, revealed that voicing one's problems, even to a stranger, can be inherently therapeutic. It's not just about receiving an answer, but the process of acknowledging and articulating the pain itself.
Floating a message. Writing down your struggles is like sending a message in a bottle; it acknowledges that someone might care and be able to offer comfort or perspective without knowing you personally. This act validates your feelings and combats the sense of being uniquely alone in your suffering.
Shared human experience. Realizing that others have felt similar pain is reassuring. Agony columns, by showcasing common anxieties, highlight that personal struggles are often part of a wider, shared human experience, making the individual feel less isolated and strange.

2. Empathy Means Understanding All Sides.

That, I feel, is the real toil of the agony aunt – to imagine what it is like for the people surrounding the agonizer.

Beyond the letter-writer. Effective advice-giving requires extending empathy beyond the person writing in. It involves trying to understand the motivations and perspectives of the friends, partners, or family members who are the subject of the complaint, even when their actions are disapproved of.
Compassionate 360 view. Delivering a compassionate view from all sides is challenging but crucial. It avoids simply validating the agonizer's feelings and instead encourages a broader understanding of the complex dynamics at play in relationships.
Exceptions for safety. While empathy for all parties is the goal, the safety of the letter-writer takes precedence in cases of coercive or potentially dangerous dynamics. In such instances, providing an alternate perspective is secondary to ensuring the person's wellbeing.

3. Societal Shame Fuels Women's Deepest Anxieties.

If I were to look at the majority of letters I get week on week and put them all side by side, the story is one of female anxiety; of not feeling good enough.

A recurring narrative. The author observes that a dominant theme in letters from women is deep-seated anxiety and a pervasive feeling of not being good enough. This manifests across different life stages, from teenage body image issues to worries about virginity, relationship status, motherhood, and aging.
Internalized pressures. These anxieties are often rooted in societal sexism and internalized shame. Women are conditioned to believe their worth is tied to external factors like appearance, relationship status, or fertility, leading to self-doubt and self-loathing when they feel they don't measure up.
Removing the shame. A key part of the author's approach is to normalize these feelings. Reminding women that their experiences are common helps to remove the shame, allowing them to focus on addressing the problem rather than feeling inherently flawed.

4. Relationships Evolve; Adaptation or Ending Can Be Healthy.

If a friendship can’t evolve as its two participants mature and change, it’s likely that they’ll grow out of it.

Growth necessitates change. Just as individuals mature, relationships must also evolve. Friendships formed in childhood or young adulthood may not sustain the same intensity or form as lives diverge, and this natural evolution doesn't signify failure but potential freedom.
Navigating transitions. Moving in together or apart can strain friendships, highlighting incompatibilities in domestic habits rather than fundamental flaws in the bond. Recognizing this might allow the friendship to return to a healthier state once living situations change.
Ending with kindness. While ghosting is cruel, a slow cooling-off or an honest, kind conversation about the friendship having run its course can be necessary. Adaptation, such as seeing each other less frequently or changing the nature of hangouts, is also a valid way for friendships to survive without ending entirely.

5. Attraction Defies Logic and Expectations.

You can’t date someone as an exercise of self-improvement, particularly when you know how much he likes you.

Beyond the checklist. Attraction is complex and doesn't always align with rational criteria or what we think we "should" want. Dating someone solely because they are a "good guy" or the opposite of a past toxic partner, without genuine attraction, is unlikely to lead to a fulfilling relationship.
Slow burn vs. none. While slow-burn attraction is possible and often leads to stable relationships, it requires some initial magnetism. You cannot force attraction where none exists, regardless of how compatible you might seem on paper or how much the other person likes you.
Finding the balance. The ideal partner is someone who is both kind and desirable. Reducing potential partners to a binary of "kind but boring" or "charismatic but dangerous" is a false dichotomy. It's possible and reasonable to seek someone who offers both fun and safety.

6. Money Talk is Awkward but Necessary in Relationships.

Money is an icky topic, even with the people who are closest to you, but it has to be talked about.

Financial disparities are common. As friends and partners progress in their careers, differences in income and lifestyle become apparent. Trying to "keep up" financially with friends can lead to embarrassment and resentment.
Unspoken issues fester. Avoiding conversations about money, whether in friendships or romantic relationships, leads to distress and misunderstanding. A frank, albeit awkward, discussion upfront can prevent future upset and build trust.
Understanding motivations. Tight-fisted behavior or constant talk of finances often stems from deep-seated fear or anxiety about money, rather than malice or boasting. Approaching the conversation with empathy can help uncover these underlying issues.

7. Parental Worries About Adult Children Are Often Misplaced.

Parental concern is one that is as much formed by primal instinct as it is objective rationality.

Instinct vs. reality. Parents naturally worry about their children, but this concern is often driven by primal instinct rather than an objective assessment of the child's life. A successful, independent adult child may still be a source of anxiety for a parent, particularly regarding milestones like finding a partner or having children.
Different timelines are valid. Applying one's own life trajectory (e.g., marrying and having children young) as the standard for an adult child's life can cause unnecessary anxiety. There is no single "right" timeline for meeting a partner or starting a family, and people find happiness on diverse paths.
Trusting their judgment. Adult children are aware of their own desires and circumstances, including their relationship status and biological clock. Parents don't need to remind them or express worry, as this can add pressure and shame. Instead, trust in their ability to navigate their own life and make choices that are right for them.

8. Family Dynamics Require Diplomacy, Not Just Agreement.

Diplomacy is a hugely underrated social skill and one that doesn’t take huge amounts of effort.

Merging families is complex. Integrating into a partner's family, especially a close-knit one, can be challenging. It requires navigating existing dynamics, inside jokes, and traditions, and can sometimes feel like an unwelcome intrusion to the established unit.
Show, don't tell. Winning over difficult in-laws isn't about proving you're a threat; it's about demonstrating respect for their place in your partner's life without needing to become a full member of their core family unit. Subtle gestures of inclusion and seeking their opinion can help.
Understanding differing views. Disagreements, even on fundamental issues like politics, are common within families. While it's important to stay true to your values, maintaining relationships with those who hold opposing views requires patience, a willingness to understand their perspective, and sometimes agreeing to avoid contentious topics.

9. Heartbreak is Profound Pain, But It Signifies Having Lived.

Grief is an electric shock that tells us we are fully alive – it means we’re connecting and creating and caring.

A unique trauma. Heartbreak is described as a uniquely devastating experience that can feel overwhelming and even lead to temporary madness. It's a pain with velocity that often spurs significant life changes or epiphanies.
Evergreen vulnerability. The capacity for heartbreak doesn't diminish with age or experience. Regardless of how many times it happens, the pain can feel just as sharp, highlighting an enduring vulnerability to love and loss throughout life.
It eventually ends. While heartbreak doesn't necessarily get easier with practice, the knowledge that it does end eventually provides solace. The pain is a sign of having deeply connected and cared, and it ultimately softens, leaving behind a sense of awe and resilience.

10. Shed Shame Around Sex and Your Past.

You haven’t failed at femininity by not withholding sex, when sex was exactly what you wanted.

Dating myths are harmful. Societal expectations and outdated dating "rules" often tell women to be less expressive, less keen, and less sexual to be desirable. These myths are unfairly gendered and create unnecessary shame around consensual sexual experiences.
Sex is not a power play. Having sex on a first date or expressing sexual desire does not mean you've "caved" or lost a power game. It can simply be a sign of chemistry and mutual interest between consenting adults.
Your past is not shameful. Worrying about a new partner judging your sexual history or past relationships is common but unwarranted. Your past consensual encounters are not a reflection of your worthiness for love and respect in the present.

11. Perfectionism and Fantasy Hinder Real Connection.

Romantics are, ironically, the worst culprits for being relationship-avoidant.

The trap of the ideal. Seeking a partner who perfectly matches a predetermined list of qualities or a fantasy created in one's mind often leads to disappointment and prevents recognizing potential in real people. This perfectionism can be a form of relationship avoidance.
Longing vs. reality. For some, the excitement of longing and the potential of an imagined relationship are more appealing than the reality of a committed partnership, which involves unpredictable flaws and compromises. This focus on fantasy hinders the ability to engage with actual people.
Embrace the imperfect. Real intimacy comes from accepting the whole person, including their downsides and quirks, rather than trying to pick and choose only the desirable traits. Letting go of rigid expectations allows for the possibility of being surprised by who you might love.

12. Self-Worth Comes From Character, Not Appearance or Validation.

The true transformation of self-esteem, the ‘you-won-t-believe-the-before-and-after’ makeover, does not come from perfecting appearance.

External validation is fleeting. Relying on external factors like physical appearance or romantic validation from others for self-worth is a precarious foundation. These external elements are subject to change and do not address the root of low self-esteem.
Build internal strength. Genuine self-esteem is built through developing character and integrity. This involves cultivating qualities like kindness, humor, curiosity, resilience, and a strong work ethic.
Character is robust. Unlike appearance, which can be affected by many variables, character is a more stable and enduring source of self-respect. Focusing on internal growth provides a solid foundation for feeling good about oneself, regardless of external circumstances or validation.

Last updated: May 8, 2025