When we own a business we meet people. Even if our business is completely online (like mine), most of us will have some form of interaction with other humans. The more contact we have with certain people — associates, collaborators or clients — the greater chance there is for us to build rapport with them. But should we ever ask a client out?

Short answer: Heck, yes!

If you have a great business model, there will always be another client, but it’s incredibly rare to find someone who sets your soul on fire.

Okay, that’s great, Anna, but how do we really know if this person is “the one?”

Great question!

We don’t know. At least not right away, because as many are aware, attraction doesn’t equal compatibility.

Potential Outcomes of Asking a Client Out

  1. He or she will say, “No, thanks.” (Oops, you read that rapport wrong!)
  2. They’ll say, “Yes” and you’ll have a short lived romance and possibly lose a client.
  3. You’ll fall in love and have a 50% chance of living happily ever after. (According to divorce rates.)


The above possibilities are no surprise. So, is it worth asking out a client? And if yes, how do you do that?

Again, my short answer is that it is worth the risk if you think there’s actual mutual attraction.

How do I know if there’s mutual attraction, Anna?


Signs of Attraction

Does the person that makes your heart pitter-patter:

  1. Frequent your business more than necessary? Sure, they may be disorganized, but they might also want to interact with you because they’re attracted.
  2. Linger longer (in person or on the phone or IM) and show extra interest in you (and no one else)? Again, they might be a chatty Cathy / Charlie — or they might like you “that way.”
  3. Smile a lot, laugh a lot and / or tease you playfully? Ok, perhaps they’re an Aries. (Ask them! That’s a great conversation opener, by the way.) If they’re an Aries, check for other signs, if they’re not of the Ram astrological sign, they might just dig you!
  4. Ask about your personal life? Particularly, do they lead the conversation into revealing your relationship status?
  5. Do they give you physical compliments? If someone is physically attracted to you, they’ll notice your physical qualities first. Though, if they do, it’s still not a guarantee that they’re interested romantically. Some people are just good at giving compliments.

These are some signs of potential attraction. But the best way to find out is to ask the client out!


How to Ask Out a Client

There are two ways to ask out a client — soft and subtle or big and bold.

Remember, you may get rejected with either approach, and yes, you may lose a client — oh, well!


Soft and Subtle

“You, Joyce (/Jim), I’ve really enjoyed our chats but I don’t feel I know you very well. Boomer Jerritt is having an exhibition for his Antarctica works this weekend. Is that something you might want to go to?” (It’s implied that you mean with you.)


Big and Bold

“Joyce (/Jim), whenever we chat my day gets brighter. I know this may be inappropriate because you’re a client, but I’d really love to get to know you better. Would you like to go out sometime?”

Yep, you got that right, ladies can ask a man out the same dang way. Women’s lib, y’all. But not to get too feminism-fistic, I’d advise that ladies deliver this line playfully with a bit of cheekiness — men and women are wired different biologically. Don’t shoot the messenger! (Me.)

It goes without saying that you’ve got to choose a good time to ask. There are too many variable to cover this here but if you’re a dentist, don’t ask your client out while they’re in the reclining chair numb and drooling. (Though that would make a great story at a wedding.)

Worst case, you flattered someone. The worse case is not that you lose a client. A client can be replaced, finding love is more difficult.


xo AJ

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