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How To Approach A Coworker Crush (2022 Edition)

approaching women Feb 03, 2022
Woman and man seated at desk together, woman smiling at the man

Have a crush on your coworker?


I'm genuinely enthusiastic about you exploring a romantic relationship with a coworker.

💑 Dating at work is natural, and common for many reasons:

  1. Time spent at work. Many of us spend more than half of our waking lives at work. How else are you meeting women?!
  2. Colleague commonalities. You and your coworker are likely to have similar values, interests, and lifestyles given you work together.
  3. Many well known couples linked at work. Barack & Michelle Obama are just one famous example.
  4. It's better than alternatives. Would you rather tell people you met at work, or on Tinder, or at a bar?!

Don't believe me? According to this 2018 survey of 2,000 workers, 36% reported dating a colleague!

☝️ There are right and wrong ways to approach a colleague though.

If you want to successfully convert your professional relationship with a woman into a romantic one, you need to do 3 things:

  1. Mitigate risk 🦺
  2. Ask appropriately ☑️
  3. Proceed thoughtfully 💡

Read on for details!




Before You Approach, Mitigate Risk 🦺

Man and woman seated at a coffee shop next to a computer, with woman smiling at man

You wouldn’t be reading this guide if you weren’t already aware that approaching a colleague comes with added risk.

Specifically, there’s risk of:

  • 🥀 Emotional consequences like persistent discomfort at work if things crash & burn romantically but you have to maintain a close professional relationship;

  • 🗣️ Reputation harm if your relationship results in gossip or distractions at work for your other colleagues;

  • ⚖️ Conflicts of interest where a romantic relationship could compromise your (or her) judgment in a business setting;

☝️ Because of these risks, many women are reluctant to date colleagues.

What does this mean for you?

You’ll maximize your likelihood of success by mitigating these risks before you make your move. This way, when you approach:

  • ❌ She’s not worrying about the downsides of dating a colleague 
  • ✅ She’s able to evaluate the upside of dating you without your work relationship working against you 

🤝 To mitigate the risk of emotional consequences, be her friend first.

This might sound like bad advice if you’re paranoid about the friend zone.

(And if this is you, check out my post on how to get out of the friend zone here!)

But you’ll truly have an easier time transitioning your relationship from professional to romantic if you're friends.

Friendship will make her feel confident:

  • ❤️ You genuinely care about her
  • ☀️ You’re motivated by your connection with her, not your ego or another factor
  • 👼 You won’t be a nuisance if things don’t work out

Don’t have a friendship with her already? Build one!

Just make sure it’s genuine.

If you nominally engage her to be friends, but you’re angling for romance too soon (e.g. you propose a candle-lit dinner as your first 1:1 hang-out...)

She’ll catch on, and be turned off ðŸ¥€

To mitigate the risk of reputation harm, demonstrate discretion.

Even if she’s not consciously aware of it...

Your crush won’t date a colleague she associates with office gossip and drama.

This is intuitive: she’s terrified of the idea that her private life could become the office topic du jour someday ðŸ˜¬

Avoid gossip and drama, especially with her.

Want to know if she trusts you?

A good test is if she's ever told you a secret.

If yes, you’re in good position to proceed! If not, you’ve got work to do ðŸ˜…

Man and woman at coffee, enjoying a laugh together

⚠️ To mitigate the risk of conflicts of interest, use extra caution if your work is interrelated.

Most experts will say dating within your chain of command, for example:

  • Dating a direct report â¬‡ï¸
  • Dating your boss â¬†ï¸ 

… is 100% off limits due to potential conflicts of interest (e.g. you might inappropriately advocate for your partner’s promotion).

I’m unconvinced that dating a direct report is never OK.

  • First, I know too many women who happily married a former boss (and one who happily married her direct report!) without creating a problem at work to believe this is inherently inappropriate 🤵‍♂️

  • Second, the point is moot — if you’re romantically interested in a direct report or your boss there’s already a conflict of interest regardless of whether or not you actually end up dating!! 🤷

Still, the more interrelated your work, the more careful you need to be.

Particularly if your crush sits in your chain of command, there can be serious consequences if you fail to follow your company’s relevant policies, and the wrong person catches wind.

So, if your crush is in your chain of command:

  1. Study your company’s relevant HR policies 📝
  2. Think carefully about the risks 🧠
  3. Hatch a plan that’s respectful to all parties 🧑‍⚖️

In the case of a direct report (or boss), you might be wise to NOT make a move until you’re out of each others’ chain of command…

Or, you may just want to proceed extra carefully and methodically…

Use good judgment, err on the side of caution, and remember there’s no hurry.

If it’s meant to be, you’ll find a way.

And if you don't want to deal with any of these workplace romance risks, check out my general guide on how to meet women!




Ask Her Out Appropriately â˜‘️

Couple seated outside in front of a computer

Once you’ve laid the groundwork to mitigate concerns about dating a colleague, you can more confidently make your move.

How do you actually make your move?

Below are my four best practices to:

  • Maximize the likelihood she reciprocates your feelings ðŸ“ˆ
  • Minimize downside if she doesn’t ðŸ“‰

1️⃣ First, communicate in-person wherever possible.

Slack, Teams, email, and SMS are all OK mediums for building a friendship with a colleague (and perhaps your only options if you're working remotely)...

But they’re not OK for initiating romance. You need to do that in-person ðŸ“

If you’re ready to make the jump, wait until the next time you’re physically together.

If you're not seeing each other in-person already... this is exactly why you need to build a friendship first!

Invite her to walk or get coffee & catch up in a friendly way to get the ball rolling â˜•

2️⃣ Second, follow a “one strike & you’re out” rule.

Both Facebook & Google have adopted “one strike & you’re out” workplace romance policies that state:

  • ✅ It’s OK to ask a colleague out once…
  • ❌ But if they say no, don’t ask again.

I’m a huge fan!

“One strike & you’re out” helps mitigate the risks we discussed earlier, and it forces you to be thoughtful about when and how you swing.

Note the “one strike & you’re out” rule applies to both:

  • 👩‍❤️‍👨 Explicit romantic escalations that we're discussing here (e.g. “we’ve been friends for a while, and I’ve been starting to feel…”)
  • ☕ Outings as friends that you might use as forums to initiate a romantic connection (e.g. “want to grab coffee sometime?”)

If she isn’t keen on meeting up for coffee without romantic undertones, she’s definitely not keen on romance!

So resist the urge to try again if she doesn’t say “yes” the first time.

3️⃣ Third, if she doesn’t say YES, assume she means NO.

This is another Google & Facebook workplace policy I love, and recommend clients adopt for both inside & outside the workplace.

What does it mean?

If you approach a colleague (or in my opinion, any woman) and she doesn’t directly take you up on your offer (e.g. “let’s do it!”)...

You should assume she’s not interested & move on.

This means there’s no gray zone. Treat ambiguous responses like “no.”

For example:

"That sounds nice, but I'm really busy with work currently, so I have to pass."

"Ah sorry I’m out of town!"

"I can’t right now, sorry."

… all mean “no” because the woman

☝️ Like the “one-strike” rule, the “anything but yes means no” rule applies to both explicit romantic advances, and friendly overtures to hang out.

Seem too extreme?

It’s not once, you understand the rationale.

Man making kissing face, and woman frowning

Many women are bad at turning guys down.

Saying “no” is awkward, and we fear saying it will hurt guys’ feelings...

So often when we want to say “no” we chicken out, and use a softer & narrower excuse like “I’m busy tonight.”

Aside: I hate that many women pussyfoot around “no” because it inevitably leads to discomfort on both sides:

  • Women hope in vain that guys will “get the message” 🙄
  • Men hope in vain that women are into them, excuse aside 😬

Regardless, women’s aversion to “no” is a reality of dating.

So “anything but yes means no” is a useful rule to adopt to avoid wasting time and energy on women who aren’t interested ðŸ˜” 

It almost goes without saying, but to be clear, if she responds like:

"I can’t tonight, how’s Tuesday next week?"

… she’s saying “yes.”

Her intent is clear if she attempts to reschedule 💓 📅

But if she says something like:

"I can’t tonight, maybe another time!"

… she still means “no” regardless of how much you wish “maybe another time” actually meant “you ask again” 😕

However, as *bad* as women are at communicating when they *aren’t* interested...

Women are *good* at communicating when they *are* interested!

If she’s into you, you'll usually know it.

And if you don't know it, check out these signs she's developing feelings for you.

👩‍❤️‍👨 Finally, make sure she knows that YOU know what you’re getting into.

What I mean is that, when you make your move, communicate two things:

  1. How you feel ❤️
  2. That you recognize and respect the considerations stemming from your coworker relationship 👔

This doesn’t mean you need to sit her down for a formal “define the relationship”-type conversation...

But whenever and however your relationship takes its turn toward romance...

You’ll increase the likelihood of success if she knows you appreciate the sensitivity of the situation.

Saying something lightweight, like the following, can do the trick:

"I’d like to explore a romantic relationship with you!

No matter where this goes, though, know that I’ll do my best to be respectful of our professional relationship."

This is short, sweet, and to the point. It communicates that you know what you're doing.

Stepping back, there are a number of different routes you can take to arrive at the point this is relevant.

Maybe you:

  • Have been friends outside of work for a while ðŸ‘«
  • Hang out regularly ðŸ“† 
  • Drunkenly made out after “one drink” at happy hour turned into six ðŸ’

Or maybe you:

  • Are still getting to know each other ðŸ†• 
  • Had fun both times you’ve hung out 1:1 as friends ðŸ‘«
  • Want to test the romantic waters by asking her on a dinner date the next time you meet 🛶

No matter what, you won’t regret assuring her she doesn’t need to sweat your professional relationship.




Proceed Thoughtfully ðŸ’¡

Man and woman seated at a coffee table, both smiling, where man is pointing at a phone the woman is holding

Once you’ve communicated your feelings, and she’s reciprocated your interest...

Congratulations! The hard part’s over.

Here are three last tips for success.

☢️ FIRST... Keep it away from work until you can't.

At least at the start, the less your other coworkers know about your budding workplace romance, the better:

  • Extra attention can be a distraction both from work, and from building a stable romantic relationship 👀
  • More people in-the-know means more awkwardness if things don’t work out between the two of you 🤕

An easy solution is to keep pronouncements on a “need-to-know” basis.

For example, if your company’s policies require you to inform HR about an office romance, you should tell them. But:

  • Don’t jump the gun. A first or second date probably doesn’t meet your HR reporting threshold, at least in spirit 🤫
  • Chat with your partner first. She may have different feelings about your communications strategy, and her opinion matters 💁‍♀️

🐢 SECOND... take things slow.

I won’t harp on the risks of a workplace romance further. Just remember there’s no need to rush.

If things work out, you’ll have a full lifetime together 👴👵

No matter how eager you are to explore your new romantic relationship, you can afford to take the time to feel like this is the right fit before escalating things.

You won’t regret it.

🎉 THIRD... remember to have fun!

You deserve it 😃




Recap & Next Steps

If you’re crushing on your coworker, follow these 3 steps to make the romance a success:

  1. 🦺 Mitigate risks before making a move. In particular, you dramatically increase your chances by being a friend first.

  2. ☑️ Ask appropriately. Test the waters in-person (not online), signal you respect your relationship as coworkers, and follow “one-strike-you’re-out” and “anything-but-yes-means-no” policies.

  3. 💡 Proceed thoughtfully. Keep pronouncements about your new relationship to the necessary minimum, take things slow, and (most of all) have fun!

- Blaine


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