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The clearest supported order for Tony Soprano’s principal named affairs is Irina Peltsin, Gloria Trillo, Svetlana Kirilenko, and Valentina La Paz. That is a partner-level outline, not a verified list of every sexual encounter: brief and unnamed hookups are not exhaustively documented in the available episode references. Julianna Skiff belongs in a separate near-affair category because the relationship is described as unconsummated.
The named affairs, in broad order
The sequence below reflects the broad chronology supported by episode-guide and character-summary references. It is not an episode-by-episode audit, so it should not be read as a definitive dating of every encounter.
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Irina Peltsin
Irina is identified as Tony’s long-running relationship beginning in the pilot. Secondary analysis places its end around the second-to-last episode of season two; those bounds are a guide to the chronology, not an official episode-level record. Her later call to Carmela, in which she reveals Tony slept with Svetlana, makes her affair consequential well beyond its own span.
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Gloria Trillo
Tony’s affair with Gloria takes place in season three. Episode-guide summaries describe a relationship that turns sour, but the references available here do not establish a more exact start-to-finish chronology.
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Svetlana Kirilenko
Tony’s sexual relationship with Svetlana, Irina’s cousin, comes to Carmela’s attention through Irina’s disclosure. The revelation contributes to the separation and marital confrontation at the end of season four.
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Valentina La Paz
Valentina is also identified among Tony’s named mistresses, and the surfaced summaries place her later than Gloria. The available references do not establish a more precise position by episode, so a narrower placement would require checking the episodes directly.
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Why “every time” cannot mean every encounter
There is no reliable exhaustive count in the available episode-guide and character-summary references. They mention brief encounters and women at the Bada Bing as well as recurring relationships, but do not provide a complete scene list. The four names above are therefore best understood as the principal named affairs supported by those references—not a total of every time Tony was unfaithful.
Julianna Skiff was a near-affair
Tony’s attraction to Julianna Skiff is often relevant to a list of his romantic pursuits, but it should not be counted as a confirmed sexual affair: secondary summaries describe him backing away and the relationship as unconsummated. Separating her from the affairs keeps the chronology from treating an almost-affair as an established sexual relationship.
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What the affairs mean for Tony and Carmela
Tony’s infidelity contributes to major ruptures in the marriage, but Carmela’s awareness and response are not a single, uniform reaction. A scholarly discussion describes her as aware of Tony’s sexual escapades, while episode summaries show particular revelations driving conflict. That supports saying the affairs affect the marriage; it does not establish that Carmela knew every detail or every instance.
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