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An active member of FZY, he spent his gap year in Israel with the organisation.
And it was Israel which influenced Londoner Simon's choice of course at Birmingham University and the London School of Economics, where he studied international relations and politics, focusing on the Middle East Arab-Israel conflict.
While at Birmingham, Simon served as Union of Jewish Students Midland region chairman and was a member of the national executive.
On his graduation, he went straight into Jewish communal work, serving as British Aliyah Movement co-ordinator.
From there he advanced to become Board of Deputies public affairs officer in 2000 when the second Intifada broke out.
He said: "I was there when the entire media and Jewish community were going berserk."
It was there that Simon learned how to control his emotions and strong political feelings so that he could deal with people across the political divide.
He says: "Although the topic of Israel is very close to my heart, I try not to talk about my personal feelings and views."
Five years ago, Simon left the board to fulfil his dream of making aliyah.
But even there, living in Jerusalem and now in Modiin which he calls "Israel's Milton Keynes", he still kept his very strong connection with British Jewry.
His first position was for the British Israel Communications and Research Centre, writing their daily press briefings.
Rising at 6am (4am British time), he would quickly scan all the British and Israeli English language press, looking for their Israel coverage.
He said: "I did it solidly every day for 18 months. Even on holidays I used to take my laptop with me.
"After a time, it starts to grind you down, looking at bad news all the time."
The monotony of his repetitive work was broken when he was called up to serve as an IDF spokesman for three months.
He continues to serve his reserve duty at the Foreign Media and Jewish Organisations desks.
His next position was as managing editor of the NGO Monitor, which monitored the roles of non-government organisations in the Israeli-Palestinian conflict.
In 2004, he married Rhea and they settled in Modiin. Simon says: "We must be the only ones without children in the city. It is real suburbia."
Last year, he joined Honest Reporting - an organisation founded in 2000 by a group of British university students who were dismayed by the anti-Israel slant of so much of the British media. They organised email protests to offending publications and built up a database of subscribers.
Realising that they needed professional input to their website, to build up their subscriber base and develop materials, the volunteers handed Honest Reporting over to Aish HaTorah, who spread its influence.
In 2003, it became independent, setting up branches in Canada, the US, Israel and - last March - Britain.
Honest Reporting now has 140,000 subscribers, 3,000 of whom are in Britain.
So, having survived all the adverse media coverage of the English-speaking press, how is Simon finding coverage of the current hostilities?
He said: "Surprisingly, this is one of the rare times that we have had press support.
"Israel has had a lot diplomatic cover from the USA, UK and EU."
He added: "I think Israel did very well getting its message in answer to the charge of disproportionate response."
But he warned: "This is about to change with the pictures of civilian casualties coming out of Lebanon.
"Because Hezbollah are positioned in civilian areas, the pictures are very powerful.
"These are liable to sway the public and we could lose our initial support."
Which means that Simon will have to work all the harder to rebut all the expected criticism.
But, he adds, so far the Israeli public, including those hiding in shelters, is solidly behind its government.
This summer Simon will certainly have his work cut out. It is fortunate that he took his belated honeymoon earlier in the year.
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