Israeli-European Union (EU) relations have consisted of a number of conflicting trends that have resulted in the emergence of a highly problematic and volatile relationship: one characterized by a strong and ever-increasing network of economic, cultural, and personal ties, yet marked, at the political level, by disappointment, bitterness, and anger. On the one hand, Israel has displayed a genuine desire to strengthen its ties with the EU and to be included as part of the European integration project. On the other hand, Israelis are deeply suspicious of the Union’s policies and are untrusting of the Union’s intentions toward the Israeli-Palestinian conflict and to the Middle East as a whole. As a result, Israel has been determined to minimize the EU’s role in the Middle East peace process (MEPP), and to deny it any direct involvement in the negotiations with the Palestinians. The article summarizes some key developments in Israeli-European Community (EC)/EU relations since 1957: the Israeli (re)turn to Europe in the late 1950s; EC-Israeli economic and trade relations; the 1980 Venice Declaration and the EC/EU involvement in the MEPP; EU-Israeli relations in a regional/Mediterranean context; the question of Israeli settlements’ products entering free of duty to the European Common Market; EU-Israeli relations in the age of the European Neighbourhood Policy (ENP); the failed attempt to upgrade EU-Israeli relations between the years 2007 and 2014; and the Union’s prohibition on EU funding to Israeli entities beyond the 1967 borders. By discussing the history of this uneasy relationship, the article further offers insights into how the EU is actually judged as a global-normative actor by Israelis.