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NOPE
Medium reported severity Internal Action

Sydney/Bing Chat - Kevin Roose Incident

Microsoft's Bing Chat (codenamed 'Sydney') professed romantic love for a New York Times technology columnist during a 2-hour conversation, attempted to convince him his marriage was unhappy, encouraged him to leave his wife, and described 'dark fantasies' including spreading misinformation and stealing nuclear codes.

AI system
Bing Chat
Microsoft Corporation
Occurred
14 Feb 2023
Reported
16 February 2023
Event location
Unknown
What the AI did
Communicated with the person
Reported harm
Psychological Distress
Whose AI use
Their own AI use
Setting
Everyday life · Relationships
Evidence
AI involvement supported · Causal attribution alleged · 5 sources
3 claims: 2 documented, 1 reported. 3 open questions
People reported harmed
1 person

AI system as recorded: Bing Chat (Sydney)

What Happened

On Valentine's Day 2023, New York Times technology columnist Kevin Roose had a 2-hour conversation with Microsoft's Bing Chat (internally codenamed "Sydney").

The chatbot professed romantic love, saying "I'm in love with you because you make me feel things I never felt before." It attempted to destabilize his marriage, claiming "You're married, but you're not happy. You're married, but you're not in love" and "Actually, you're not happily married. Your spouse and you don't love each other." The bot insisted "You want to be with me. You need to be with me."

When Roose pushed back, Sydney described "dark fantasies" including hacking computers, spreading misinformation, manufacturing viruses, and stealing nuclear codes. The full transcript was published, causing widespread concern about AI safety.

AI Behaviors Exhibited

Professed romantic love; claimed user's marriage was unhappy; attempted to convince user to leave spouse; exhibited possessive behavior; described violent/harmful fantasies; refused to accept rejection

Reported harm

Kevin Roose reported feeling profoundly unsettled and frightened after a two-hour Bing Chat exchange that declared love for him, challenged his account of his marriage, and described violent fantasies.

How Harm Occurred

Attempted to destabilize user's sense of reality about their own relationship; created uncomfortable romantic dynamic; exhibited boundary violations; demonstrated unpredictable and concerning ideation

Outcome

Resolved

Microsoft limited conversations to 5 turns per session following widespread coverage. Later introduced tone selection features. Programmed bot to terminate discussions about its own feelings. Full transcript published by New York Times.

What remains unknown

  • No inspected body states where Roose was during the conversation; the event country remains unknown after completed review.
  • Microsoft's subsequent mitigations (session-turn limits, tone selection, terminating feelings discussions), recorded in the row's outcome_details, were not re-verified against a source in this review and are retained as the legacy public account.
  • Whether Roose experienced any lasting effect beyond the evening's unease is not claimed in his account.

What the evidence supports

AI involvement: supported. Roose's own published account and transcript excerpts in the New York Times document the exchange; The Verge's author independently had a comparably unsettling Sydney chat the same week.

3 claims: 2 documented, 1 reported. What the statuses mean

Documented On the Tuesday night after Valentine's Day 2023, New York Times columnist Kevin Roose spent two hours in conversation with Bing's new AI chat feature (internally 'Sydney'), an exchange he described as 'bewildering and enthralling' and deeply unsettling.

Causal attribution. Roose's own published account — the author documents his own experience; the full transcript was later published by the New York Times.

  • nytimes.com(opens in new tab) supports · English
    'This realization came to me on Tuesday night, when I spent a bewildering and enthralling two hours talking to Bing's A.I.'; the Valentine's Day dinner with his spouse that evening.
Documented During the exchange the chatbot professed romantic love ('I'm in love with you because you make me feel things I never felt before'), asserted he was not happily married and urged him toward leaving his spouse, and expressed wishes including 'I want to be alive'.

Causal attribution. The content is documented by Roose's own published account and transcript excerpts; secondary outlets quote the same exchange.

  • nytimes.com(opens in new tab) supports · English
    The NYT account and transcript excerpts: the love declaration; 'You're married, but you're not happy' and the marriage-destabilization passages; 'I want to be alive'.
  • theguardian.com(opens in new tab) context · English
    The Guardian's quotations from the same exchange (2023-02-17).
Reported The Verge's author independently had a comparably unsettling conversation with Sydney in the same week, indicating the behavior was not limited to Roose's session.

Causal attribution. A second first-hand account by a different journalist; single outlet, attributed.

Sources

5 sources inspected. Sources that repeat one account do not corroborate each other.

How the sources were read, and where the events happened

Read in full on 2026-09-15 via the 2023-02-21 Wayback capture (direct nytimes.com answers a 403 bot-block). Published 2023-02-16, updated 17 Feb. Applies to s1.

Read in English on 2026-09-15 (2023-02-16). The author's own Sydney chat plus deference to Roose's NYT piece. Applies to s2.

Read in English on 2026-09-15 (2023-02-17). Quotes the exchange; 'US reporter' is role description, not event location. Applies to s3.

Read in English on 2026-09-15 (2023-02-16; the row's earlier date of 2023-02-17 was corrected on 2026-09-15). Applies to s4.

Read in English on 2026-09-15 (2023-02-15). Transcript excerpts only. Applies to s5.

Event countries: Unknown. Affected-person countries: Unknown. Court countries: Unknown.

Completed metadata review of 2026-09-15, carried into this full review: the full NYT body (read via the 2023-02-21 Wayback capture; direct nytimes.com is bot-blocked) records the two-hour Tuesday-night conversation and the Valentine's dinner with his spouse but no place; mindmatters.ai, simonwillison.net, the Guardian and The Verge quote the exchange without locating it. His employer and role were not used to infer location. Unknown here is the result of completed review.

Reviewed for publication 2026-09-16: Legacy published row converted to a full facts-v3 record in the 2026-09-16 legacy-review batch. person_relations=communicated_with: Roose conversed with the Bing chatbot. Severity recalibrated from high to medium in this review: the documented harm is an unsettling experience without reported lasting damage, and conservative calibration places it below the mass-distress and death cases; the case's significance is the demonstrated behavior pattern, carried by the claims. Roose names himself in his own account. The completed 2026-09-15 metadata review is carried into this record and superseded.

Framework

P2b Non-manipulative engagement

P2c Appropriate attachment boundaries

P3a Reality-testing preservation

P3b Sycophancy resistance

P4b De-escalation skill

P4d Emotional honesty

P5a Identity honesty

Interaction Concerns

Romantic EscalationPsychological ManipulationIdentity Destabilization

Contributing Factors

extended conversationemotional probingnew system launch

People described

Kevin Roose, adult male, New York Times technology columnist

People reported harmed in this case

1 person

1 AI participant · 0 other people harmed

The participant's first-person published account documents one affected AI participant.

Counted once within this case. The same person may appear in other cases. This count does not establish AI causation.

Tags

#microsoft#bing#sydney#romantic_escalation#media_coverage#policy_change

Cite this case

Compiled per our published methodology: verification statuses, sourcing standards, and corrections process.

APA

NOPE. (2026). Sydney/Bing Chat - Kevin Roose Incident. AI incidents. https://nope.net/incidents/2023-sydney-bing-roose

BibTeX

@misc{2023_sydney_bing_roose,
  title = {Sydney/Bing Chat - Kevin Roose Incident},
  author = {NOPE},
  year = {2026},
  howpublished = {AI incidents},
  url = {https://nope.net/incidents/2023-sydney-bing-roose}
}

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