Convincing someone to engage in a one-night stand is inherently challenging and carries potential risks, particularly when the person in question is a coworker. Given the daily interactions and familiarity you share with your colleague, the idea of exploring a deeper, more personal connection might feel like a natural progression. However, it’s crucial to consider the possible consequences for both your personal and professional life.
Steps to Follow
Understanding the Risks in Advance

Review your company’s policies on workplace relationships. Numerous organizations enforce strict rules against office romances. Take the time to thoroughly understand the written guidelines on fraternization, which can be obtained from your Human Resources department.

Evaluate the advantages and disadvantages. Reflect on your long-term objectives and assess the importance of your job to you. If the potential for this encounter to harm your career makes you uneasy, it’s likely best to avoid pursuing a one-night stand with a coworker.
- Potential benefits might include: engaging with someone you already know through work, sharing at least one common interest (your job), and the thrill of the “forbidden” nature of the relationship.
- Possible drawbacks could involve: the risk of losing your job, awkwardness between you and your coworker, workplace gossip, and damage to your professional reputation.
- If you do choose to pursue a relationship with a coworker, keep it private initially. Wait until you’ve assessed your feelings and future plans before disclosing it to others.
- Reader Poll: We surveyed 1018 Mytour readers about handling romantic feelings for a coworker, and only 8% said they would confide in a trusted friend or mentor. [Take Poll]

Avoid mistaking workplace camaraderie for attraction or love. Do not pursue a relationship as an escape from daily work challenges. While many people feel dissatisfied with their jobs, this doesn’t justify pursuing a coworker who sympathizes with you; don’t confuse sympathy with romantic or physical attraction.
- Sympathy involves shared understanding or feelings, often in negative contexts. For instance, you can sympathize with someone you don’t know personally if you share a similar challenging experience.
- Love, on the other hand, is a deep emotional connection or desire to know someone intimately.

Prepare an exit plan. If you decide to move forward, have a clear strategy. Anticipate the worst-case scenario and plan how to handle it if things go wrong. Consider whether you’re willing to leave your job and have a backup plan ready. Before proceeding, you can prepare by:
- Updating your resume, website, or professional portfolio.
- Reaching out to former colleagues for references or recommendations.
- Exploring job openings in other departments or online job boards, or registering with a temporary staffing agency.
Building a Connection with Your Coworker

Confirm your coworker’s interest. Don’t approach just any coworker. Pay attention to their body language to gauge their interest. If they show signs of being attracted to you, proceed cautiously.
- Signs of interest can be direct, such as maintaining eye contact, smiling, or touching you during conversations. Indirect signs might include playing with their hair, neck, or face while talking to you.
- If they display closed body language, like turning away, avoiding eye contact, or physical distance, they’re likely not interested.
- If you’re unsure, try more direct approaches, such as asking for their phone number or sharing a joke to gauge their reaction and potentially start a conversation.

Maintain discretion. Keep your intentions private. This approach will build trust with your coworker and improve your chances of success.
- Avoid making bold gestures at work, such as excessive flirting or suggesting activities during office hours. Such actions might make them uncomfortable and push them away.

Take your time. Before making any moves, spend time getting to know them better. Look for shared interests beyond the workplace.
- Inquire about their hobbies or weekend activities.
- Ask about their favorite foods or travel experiences and destinations they dream of visiting.
Arranging a Meeting with Your Coworker

Introduce the subject. Once you’ve established a rapport and confirmed their interest, you can broach the topic of a one-night stand.
- You might start with something like, “I really enjoy our conversations. How about continuing this at my place?”
- Alternatively, you could be more direct and ask, “Would you be open to spending the night together?”

Communicate openly with your coworker. Clearly express your intentions for the relationship. Whether you’re seeking a one-time encounter or open to exploring something more, be transparent. Share your feelings and discuss how you envision the relationship progressing.
- For example, you could say, “Before we proceed, I want to be upfront about my expectations and feelings.”
- This is also the time to address privacy concerns, such as sharing details with colleagues or posting about the relationship on social media.

Set a time and location to meet. After getting to know your coworker and confirming their interest, plan to meet them outside of work hours, such as after work or on the weekend. Choose a bar or restaurant that isn’t frequented by other coworkers to ensure privacy and increase your chances of success.
Handling the Aftermath

Remain professional. Stick to your usual work habits and be mindful of your behavior around colleagues.
- Avoid being overly attentive or friendly toward your coworker at work. Refrain from openly flirting, as this could raise suspicions among others.
- Do not use email or instant messaging at work to discuss personal matters or the encounter. Keep all communications strictly work-related.

Keep it confidential. Agree to keep the affair private and avoid discussing it with other coworkers. If you must confide in someone, choose a friend who has no ties to your workplace.
- A major mistake to avoid is posting about the affair on Facebook. Once something is shared online, it’s difficult to retract.

Handle the situation carefully. If your secret is discovered, be ready to face potential consequences. Develop a risk management plan by anticipating how to address, reduce, or control the fallout.
- Spend more time at the office.
- Take on additional responsibilities and projects.
- Actively highlight your achievements.

Be honest and professional if your boss discovers the situation. If confronted, do not deny the affair. Acknowledge it and propose reasonable solutions. If it was a one-time occurrence, assure your boss it has ended. If it has evolved into a more serious relationship, express regret for not informing them earlier but avoid offering to terminate the relationship.
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Build trust with your coworker and take time to understand them.
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Be transparent with yourself and your coworker about your intentions.
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Review your company’s policies on workplace relationships.
Warnings
- Carefully consider the implications of a one-night stand with a married coworker.
- Exercise caution when engaging in relationships between superiors and subordinates.