One thing my clients ask me a lot is how to ask out a co-worker. Seems like an easy thing to do, right? Turns out, not exactly. Take this email I received as an example:

Hey Em — So how do I ask her out if I’m not allowed to? Technically it’s against our organization’s policy. Should I just try to connect as friends? By the way, she’s in CA, and I’m in TX.

Lots of times, the company you both work for, or the group you’re a part of, doesn’t allow its employees/members to date. Or, they might discourage it so much that you’re afraid to “buck the system.”

It’s a tough situation, but here’s what I say: When it’s against policy to ask out a co-worker, you’ll need to use a basic pull method.

With a pull method, you do things to motivate a person to come to you. This is different than a push method, where you directly approach them.

So when you try to attract someone in dating, pull methods are more subtle. They entice the person into wanting to get to know you. By the end, the person will ask YOU for a date — without even realizing you set up the whole thing.

Don’t worry. These aren’t deceptive tactics. But they may be different than you’re used to, particularly if you’re a man. Subtle pull methods use the power of feminine energy and can be practiced by anyone to influence situations that need a softer touch.

Since you can’t directly ask this person out, pull methods are the way to go.

So let’s talk about some tactics you can use when you’re figuring out how to ask out a co-worker. Assuming the person is single, doing these things will naturally make them curious about you.

(Remember: Being aggressive with a date invitation mostly likely won’t work, especially if the other person is likely to get in trouble for breaking policy as well.)

How to Ask Out a Co-Worker with These 4 Steps

Escalate to a Phone or FaceTime Call

Especially in the case of my client who was interested in someone out-of-state, texting that person seems tempting.

Or, even if they’re not far away, you might want to text them anyway because it’s easier (and more discreet in your work/group environment).

But if you want to really get to know this person, texting won’t be enough.

So how do you spark a meaningful conversation with a co-worker when you’re both… well, working?

Use work (or whatever group you’re both in) as a springboard.

Ask them questions like, “What motivated you to join the entrepreneur group?” or “How’s project [fill-in-the-blank] going now that your boss just quit?”

Once you get them talking, think about how you can help. Maybe you have an idea that can work for her business or a bit of information he didn’t know that would help get his project back on track.

Whatever it is, tie that into why you should get on the phone.

For example, let’s say you’re in the same entrepreneur group. End the conversation with something like, “Would love to learn more about your business. Let’s jump on a phone call. What’s your number?”

Bam. Once they say yes, you’ve just successfully escalated the level of connection between you two. Congratulations!

Had you not done this, you would have been stuck in texting-land, where good relationships rarely happen.

Why? Texting is just too surface. Lots of people simply don’t open up that way. Conversations also tend to fizzle out too quickly.

Plus, texting always leads to miscommunication, which can kill things in the early stages of getting to know someone. Something you said sarcastically will be taken too seriously, for instance. Or, your flirtatious hints will go over their head. You can’t see their face or detect their tone, so how can you really get to know them? You can make better progress if you actually talk.

Call 3 Other People

Here’s the tricky part when it comes to strategizing how to ask out a co-worker and not break policy. Once you’ve escalated to a phone or FaceTime call, do the same thing with three other people.

I have a feeling I may lose you here, so let me be clear: You must do this. Is it a lot of work? Kind of. But it’s effective, for a couple of reasons.

Number one, because of your group/work policy, you can’t make it look like you’re singling this person out. You need to make it seem like this is just what you do. That way, they won’t feel weird about it.

In other words, it diffuses your energy. By not focusing your efforts solely on this one person, you will also come across much more relaxed and confident.

Sound familiar? This is why I always tell people to MegaDate! The practice of MegaDating — or, dating multiple people at once — diffuses your energy and builds self-esteem. So think of this as a “work” version of MegaDating. Instead of trying to get to know just one co-worker, reach out to a few of them. It will keep your special interest in this one person under wraps while allowing you to be your best self.

The second reason this works is that it keeps you from coming across too strong, which is key when you’re determining how to ask out a co-worker. It’s also true if you’re a man or woman.

As a man, coming across too strong can read as “threatening.” Sounds extreme, but women are always on guard when it comes to protecting their safety. We look for signs that a person’s crazy. We avoid things like dark parking lots and shady vibes, all to make sure we don’t get hurt. Women live with this subtle fear at all times. So especially if you’re a man trying to ask out a female co-worker, you need to make your phone call look as normal as possible so she doesn’t assume you’re some kind of stalker.

And as a woman, I hate to say it, but if you’re interested in a man, you don’t want to seem aggressive. Asking for a man’s number at work, even in today’s world, can easily look “desperate” or like you’re trolling the workplace — especially given how rare it is to talk on the phone and for women to ask men out. So connecting with other men at work too can help set the stage for “that special guy” much better.

Connect on Social Media

After talking to your co-worker over the phone a couple of times, see if you can connect on social media.

Your social media needs to help sell you. It’s another pull method that entices someone to want to know you personally. So once you guys are friendly enough, don’t hesitate to connect this way. You’ll need this tool in your arsenal.

But you have to make sure your profile’s ready first!

Basically, you want your social media account to demonstrate your value. That means you might need to beef up or edit your photos. Make sure they are all flattering. Pay attention to your profile photo and change it if necessary. You want to look your best, but not “show off.” Ease up on the cheese factor (shirtless bathroom selfies and unsolicited cleavage are a definite NO). Smile and look directly at the camera if possible.

Beyond that, it’s up to you… you may not want to aggressively edit your social just for this one person. But they will also look at your posts. Certain things will stand out, like your:

Attitude.

If your profile is filled with complaints about your job or your family, that could sway things against you.

Political leanings/interests.

Things like long, drawn-out political arguments and super-opinionated memes instantly reveal where you stand on issues. How does this compare to where they stand? Be aware that you might not be compatible in this area.

Your possible romantic connections.

If you have tons of photos with people that look like you could be dating (flirty or sexual looking poses), or even just people of the opposite sex if you’re hetero, then the person you’re interested in might not take you as seriously. This could be a negative if you want a long-term relationship.

Again, how much you edit your social media is your call. But even if you don’t change things now, keep these tips in mind. They could affect your chances with others in the future, even if this one doesn’t work out.

Plan a Trip to Their Location

When it comes to your winning strategy for “how to ask out a co-worker,” this is the most important step.

Especially if you’re in different locations, you’ll need to set this up without being awkward. So ask to see them — but be casual about it.

This is where my signature TDL method comes in.

TDL stands for “time, date, location.” You’ll need to include this in order to lock things down.

So when you ask to spend time in person, whether they’re long-distance or just a few cubicles away, be specific. Say when you want to see them and where.

Ex: I’m going to be in SF for business in February, from the 9th til the 11th. Let’s grab a coffee!

This is very different from saying “we should hang out sometime” or “let me know whenever you’re free to get together.” While these phrases can help open the door, remember you have already done that by talking on the phone, getting to know them, and connecting on social media. Now is your big moment. So hit ‘em with a TDL.

Also, notice in the example that you’re saying you’ll already be there for business. Giving a legit excuse to get together takes the pressure off and makes things casual when you want to ask out a co-worker. You don’t want to make it sound like this is a date. At the same time, you want to get them away from work so you can keep getting to know each other.

How to Ask Out a Co-Worker: Wrap-Up

So there you have it: your subtle-yet-savvy strategy for reining in that hottie at work. Are you ready to take the plunge?

If you were looking for an answer to “how to ask out a co-worker,” then I’m guessing you still might be hesitant.

After all, there’s a lot at stake. Your job or standing in the organization you’re if could be at risk if you openly date someone there. I get it.

But I have to put on my dating coach hat here and say, love is all around us. It can show up anywhere, even in formal settings.

So if someone at work really intrigues you, and you have an opportunity to interact with them, I don’t see why you shouldn’t try to encourage a relationship. You’re not doing anything wrong by using pull methods. Just make sure it happens outside the context of the organization, and you’re good.

Still, you might worry about your dating skills. Maybe you’ve never tried to connect with someone at work before. Perhaps you don’t think you’re good at dating, period.

Well, here’s the good news: No one’s good at dating. (Believe me, even I had to go on 100 dates to really figure it out… and I’m a professional coach!) We all need help one way or another, and we just keep trying to get better at it. You don’t have to wait until you’re “better at dating” or more comfortable to try these tactics. Just dive in!

Of course, if you need more help, my team and I are here. Through our matchmaking services & private and group coaching programs, we help men through these issues every day.

Through our one-on-one Zoom calls or group sessions, you will get personal coaching and hear stories from others just like you who are dealing with similar challenges. You will come away with not only the courage to ask out a co-worker, but connections that could last a lifetime.

We can work through this together. Book an intro call with me today to get started.