From Maureen Lipman's fictional Jane Lucas on Anna Raeburn's tv sitcom Agony, to the likes of Proops, Rayner, Kurtz and such American stalwarts as Dr Ruth Westheimer and Arlene Heyman, it's quite a list. So why are Jews so over-represented in the agony aunt trade.
Freeman suggests it may be a legacy of the centrality of the strong matriarchal figure to Judaism - "this person who imparts the knowledge and looks after everybody.
"Judaism goes through the mother and the mother has always had a very important role in terms of education, nurturing children and looking after the family, keeping it all together," she says.
But like any (Jewish) agony aunt worth her salt, she has more than one theory. She points out that we are a community familiar with the art of seeking an answer.
"We question, and we don't just do things that we're told, we ask why, we like to argue about everything. Discussing things and being frank are very Jewish traits."
She also reiterates a theory first advanced by Kurtz, that advice is something that Jews have held on to over centuries of displacement. "You might be thrown out of wherever you live, you might lose all your possessions, but your wisdom and knowledge and experience can never be taken away, so it's something we keep and pass down."
Kurtz is a heroine for Freeman, but most of all she admires Rayner. "She was inspiring, she just had that warmth. You could tell she'd lived, she had so much common sense," Freeman says. "I'm not going to put myself in the same bracket as those women; they had really long careers, but it is nice to be joining their ranks."
Unlike other professions, there is no obvious route in, although the skills - empathy, for one - are obvious. Rayner started as a nurse, while Kurtz came to agony aunting via a stint reporting on Vietnam. Growing up in Wembley, Freeman always knew she wanted to dispense advice, helping on a Nightline helpline as a student and taking a basic counselling course. She made it her goal after completing her journalism diploma at Cardiff.
She sees it as primarily a role for a writer. "You have to be able to research and signpost and use your initiative. Quite a lot of the job is deciphering the question - often, in the letter or email, it isn't necessarily being asked straight out."
For more serious issues such as abuse, Freeman will always seek professional expertise (in fact, she is keen to highlight the many Jewish organisations readers might not know of, and urges them to keep her updated). "You do have a responsibility, and it's not a dialogue - you've only got one chance to help." And she isn't providing an answer just for one person, but for anyone reading who might have a similar problem.
She likens the role to that of a "trusted friend" rather than a therapist, who is necessarily removed from the patient. Agony aunts need to talk about their own experiences, she says. "That's why people like Rayner became so important to readers. Obviously, you can't go through everything that your readers have been through, but you have got to have lived."
I read her an excerpt from an article Rayner wrote for the JC in 1958, advising women they'd still be able to find Jewish husbands if they became nurses. "Her hours of freedom can be spent among her own Jewish friends," wrote Rayner.
"I, for instance, meet hardly any Jewish people in the course of my work but, despite that, I have as many Jewish friends as the next girl, and I have married a perfectly delightful Jewish man."
For all that such advice seems old-fashioned, Freeman suggests things haven't moved on. "Fundamentally, we are still the same. We all want to be cared for and loved and valued," she says. "There are obviously new issues, things to do with social media, internet dating, or sexting. But the general questions haven't changed that much. Relationships that have gone stale, people having affairs, being lonely, falling out with their friends. They come round all the time."
What has changed since Proops and Rayner's time is that our first port of call in a crisis is usually Google. Freeman is doubtful this is a positive. "You go online, put a question up and then 20 people give a different answer," she says. "But none are necessarily informed opinion, some are joke answers, some are actually quite nasty." Unless you're very discerning, she says, it is challenging to find advice that will actually help.
Another change is the loss of the stiff upper lip. Britons - including British Jews - are becoming more open, thanks to increased media and popular culture discussion of personal issues such as mental health. We talk about the controversy around Helen and Rob in The Archers. Freeman, an EastEnders fan, says the spotlight offered by entertainment can only be a good thing. "It breaks down taboos and makes people experiencing similar problems feel they can speak out."
She does think being a teenager is a harder proposition now than when she was growing up, attending Bnei Akiva and then FZY tour. "When I was that age, if I had a bad day at school or had fallen out with someone, I could retreat into my bedroom and sit on the phone to my best friend, or I could read -- it was a sanctuary," she says. "Young people don't have sanctuaries any more; they've got the internet so those issues follow them home. If they've fallen out with a boyfriend, for example, they can't go on Facebook because they might see him. They are constantly tied to their phone, there's very little space to have calm."
Freeman is years away from dealing with this type of teenage angst in her own life, but having written about the subject extensively, most recently with the YA novel When I Was Me, about a girl waking up to discover her past has been erased, her advice to parents is straightforward. Do not read their texts so they think you do not trust them and do not ban them from technology and mark them out as different. "It's the same as in the past; it's about monitoring without being intrusive. It's a hard balance to get, but it's the only way of ensuring your child is safe."
She emphasises that Jewish parents -or any readers - should not assume the problems in her postbag only happen to other people, albeit that the community has good support networks.
"Even though everybody knows everybody and knows everybody's business, at the same time you really don't know what's going on behind closed doors."
She thinks the pressures - to marry Jewish, to carry on the family line - are no different from those facing other minority groups.
Growing up in a traditional United Synagogue family where she kept kosher and observed the festivals, she grappled with her faith, going through a period of being fairly devout. She now describes herself as having a strong Jewish identity, although she is not practising and her partner is not Jewish. She hopes readers will see this as an asset.
"I've been through a lot of things that people have to deal with," she says. "I understand the Jewish community and the issues that people face and I hope I can help."
Her view is that being an agony aunt is not compatible with being religious; indeed, Rayner ended up becoming the British Humanist Association's vice-president. "I always learned at Jewish school that there was a right way and a wrong way -you do it this way or you do it the wrong way. As an agony aunt, I don't condemn anything, my role is to help not to judge."
She has also dealt with her share of trauma. Diagnosed with Multiple Sclerosis at 25, more recently she terminated a pregnancy at 24 weeks because the baby had a rare chromosome disorder and doctors did not expect her to live. "I firmly believe you should prevent suffering if you can," she explains. "They told me she probably wouldn't make it to full term or would have died very young, so I had to make this decision." It was only discovered because Freeman had so many tests during pregnancy; her advice, from this and other experiences boils down to: "It's about knowing as much as possible."
She has lived with MS for 19 years, but remains well. The diagnosis had a huge impact. "Being told you have an incurable, chronic condition affects how you look at the world," she says. "When you're told you have MS you think you are going to be in a wheelchair and probably going to die, so I didn't think I had time to do anything. It made me want to seize the day."
Unsurprisingly, then, she is keen to get stuck into her new role. "It's a community that ask questions all the time," she says. "Now they've got somewhere to come for a different kind of answer."
So how would she advise some of the best-known Jews in fiction? "I'd tell Portnoy to stop masturbating so much, Shylock not to demand his pound of flesh and Ross not to cheat on Rachel during a 'break'."
Hilary's agony aunt column launches next week. If you'd like to contact her, anonymously if you prefer, email agony@thejc.com
