Whether they are handsy over dinner and drinks or keep trying to flatter, beg or bribe you into going the extra mile, boundary pushers are obnoxious and can be exhausting to deal with. While many (most, even!) clients aren't like this, unfortunately most of us will eventually run into someone who wants more than you are comfortable sharing. Some of these pushy guys can be easily redirected while others will be so bullheaded you have to show them the door. I want to share some ways you can identify and redirect boundary pushing behavior, to make the most out of those awkward encounters, and maybe even teach them a thing or two about respecting yours as well as others boundaries.

Genuinely clueless guys are rare, but they do occasionally pop up. Laying down some guidelines for how you like to be treated when he starts to step over the line typically will help eliminate any faux-pas. Sometimes it can be easy to mistake a boundary pusher for a clueless newbie, especially when a Pushy Pete is playing dumb.

A slightly more slippery type of boundary pusher is the passive aggressive one; they will try to make it seem like it’s your idea to go outside of your comfort zone when they can’t get away with playing the newbie. They may say things like “Can we try something else? What do you want to do?” “It would be so hot if I could do or see X,” or “ I want to please you/ make you feel good.” They might go past verbal manipulation to painfully obvious moves like offering massages that dissolve into uninvited touching.

Some think if they just find the right incentive you will do whatever they want, since they paid for your time and you’re here, right? Whether it is flattery or bribing you, they tend to push until you want to snap at them, especially if you have already made your boundaries known. Be firm, and remember, like a child, they may be prone to a small tantrum if you tell them “no” harshly. While entitlement issues are no fun to work around, you don’t have to put the brakes on your encounter just yet.

A few ways you can redirect these kinds of boundary pushers is to give them something else to focus on. Respond to “Can we do something different?” with “Sure, let’s take a walk,” or “Why don’t you let me return the favor?” and entertain them with tracing patterns on their back with your fingertips, or ask them to massage your hands and feet instead. When dealing with someone who feels entitled to crossing your boundaries or did not take a hint the first time you put your foot down, speak to them as you would to a youngster, as outlined in the popular book on communication, I’m OK You’re OK by Thomas A Harris, your tone and phrasing being important. An escort acquaintance once told me she often used the line “If you keep making me say no, I might forget how to say yes, and then we’ll both be sad!” This is a perfect example of a Parent to Child transaction while keeping the tone playful so she could move on from rejecting a client’s unwelcome advances to other activities she is more comfortable doing. It may sound condescending to liken it to a parent/child dynamic, but framing it this way makes it easy to maintain an air of distance and politeness when re-directing, which is crucial to running a business.

Once you are directing the energy of your interaction with your client, tell them to take off their shoes and get comfortable, ask them to pass you a bottle of water, or say what would really please you is for them to tell you a story to keep them engaged with you while gradually putting them in the mindset to follow your suggestions. Giving instructions and turning the table like this can subtly shift the dynamic away from passive aggression and entitlement from your client, smoothing out those awkward moments where you feel like a broken record.

While the vast majority of clients are respectful, lovely people, the nature of dealing in customer service (a major part of what providers do!) means dealing with folks who test the patience. While redirecting boundary pushers is one way to navigate encounters with demanding and problem clients, trust your instincts and your boundaries. Don’t compromise your feelings of safety or comfort for a client who just won’t take no for an answer, and be ready to show them the door if they will not respect your boundaries.