How to Flirt With a Coworker Remotely

Flirt with a remote coworker the same way you would in an office, only smaller. Be warm on video calls and show you remember what she tells you about her life. Add a little light teasing she can easily take as friendliness. Check your company policy first, never flirt with anyone in your reporting line, and remember that every word in work chat is a written record. The real goal is to move toward meeting her in person, at an offsite, a team meetup or a drink at a bar when you are in the same city.

Workplace romance is common. GameGlobal cites a Forbes figure that more than 60 percent of adults have had one. It still comes with rules, and remote work adds new ways to break them.

Ciaran at GameGlobal sets out three. Never make advances or sexualize anything at work, which now includes calls and chat. Read your company policy so you do not cross a line that gets you disciplined. And do not date up or down: no boss, and nobody who reports to you. A coworker on another team, at your level, is the lowest risk.

In an office, a flirty comment at the coffee machine disappears. In remote work, everything is typed, saved and searchable, and a screenshot can reach HR in seconds.

So set one test for anything you send in a work tool: could you show this to your manager without wincing? If not, do not send it. Friendly, specific and a little playful passes. Comments on her looks, late night notes and anything suggestive do not.

Remote teams still have small talk, just in different places. The chat channel for pets or music. The five minutes before a meeting starts while people wait for others to join. Virtual coffee chats. The team call where someone always forgets to unmute.

Be a visible, friendly presence in those places with everyone, men and women alike. If you only ever show up to talk to her, people will notice, and so will she.

Video is the closest thing you have to eye contact. Turn your camera on, look into it when she is talking, and react to what she says. A real laugh at her joke on a team call counts for more than any typed compliment.

When it is just the two of you on a call, take an extra minute at the start. Ask how her weekend was, and listen. Ask about the painting behind her or the dog that keeps walking into frame.

Memory is the strongest flirting tool in remote work, because it shows attention without saying anything risky. If she mentions a half marathon, ask how the training is going two weeks later. If she says her sister is visiting, ask whether they survived the weekend.

Keep it to things she chose to share. Small follow-ups like these tell her you are interested in her as a person, and she can always read them as plain friendliness if she is not interested back.

A little teasing works remotely too, as long as it is warm and about something small. "You are the only person on this team whose background is not a blank wall" is friendly. Anything about her body or her private life is out.

If she teases you back, good. If she goes flat, drop it and go back to normal.

GameGlobal suggests connecting on social media, the way coworkers often do, because it lets each of you see the other's life outside work. Follow her and a few other teammates on Instagram, not only her.

A natural reason to swap numbers helps too. Maybe you are planning a team meetup or sorting out travel for an offsite. Maybe one of you is visiting the other's city and wants a restaurant tip. Once you are chatting on your own phones about non-work things, the tone can loosen a little.

Remote flirting can only go so far. Offsites, conferences and team trips are your best chances, because everyone is there and a group dinner is a low pressure setting. Talk to her there, see whether the friendliness from calls holds up face to face, and if it does, suggest a drink, just the two of you.

If your social life runs mostly through a laptop, the skill that suffers is walking up to a woman and talking to her face to face.

The Cold Approach Bootcamp builds that skill in person and fully in the field, with live coaching on every approach and feedback after every set. It runs in Miami and New York only. Group is three consecutive days at three students per coach, and Private is 1-on-1 for one, two or three days. A total beginner is welcome, and approach anxiety is the specialty.