A Guide For Men on How To Professionally Talk To Young Women

Jon Tesser
4 min readJun 27, 2020

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Professional relationships between men and young women are fraught with a host of difficult and thorny issues. Because of this, many men miss out on enriching and rewarding relationships with women in this age group.

Luckily for me, I’ve probably had over 1,000 conversations in the past couple of years with young women in this age range. I’m proud to say that not a single one has accused me of sexual harassment, although I will admit to making the occasional slip-up (always unintended). I’ve built many enriching, rewarding relationships with these incredible young women, and I’m honored to have them in my life. I believe the feeling is mutual!

And so, given my fortunate situation, I thought I’d help out my fellow guys on some basic rules around how to have successful professional chats with the under 25 crowd.

No Mention Of Physical Appearance. Ever.

I have never, not once, in any of my conversations, mentioned anything about what a young woman looks like. I don’t compliment their eyes, or their hair, or their makeup, or anything about their appearance. Doing so would break the professional trust that we have, and give them the idea that I’m chatting with them because I view them as a sexual object. We, as men, don’t know what it’s like to be a young attractive woman, but in a lot of ways it sucks. They’re objectified for their appearance on a near constant basis, and are recognized by society (and most men, if we are being honest) solely for their looks. This rule can not and should not be broken. As soon as you mention appearance of any sort, you are no longer in “the professional zone.” So just don’t do it.

Compliments are welcome — as long as they’re not about appearance

I give out compliments to people as naturally as I drink water. This serves two purposes: I make them feel good, and I make them feel comfortable. But my compliments are about things that she has control over, and have nothing to do with her appearance. I’ll talk about her bubbly personality, her strong analytics skills, her sense of humor: anything about her character, personality, and professional skills is fair game. Young women are often insecure about their skills and are self conscious about their character, so if you’re an older man and you’re recognizing these qualities, it’s sure to boost their self esteem. Just be sure to back off if you sense that she’s uncomfortable with you saying nice things as a way to get something from her. You must be coming from a genuine, as opposed to a “needy”, place.

Recognize the power differential by treating her like a person

Let’s face it: as an older man in a power position, you might be a bit scary to her. You’re well versed in the world, have more experiences than her, and have more power vested in you by society, than she does. So there’s clearly a power differential that you need to recognize.

One of my keys to success is to equalize the relationship. I’ll do this by letting her know that I keep things casual, and I’ll often make self deprecating remarks at the beginning of conversations to put her at ease. I try and keep the mood extremely light and breezy. This helps to calm her nerves (if they’re there), and to let her know that I’m interested in a human to human conversation (as opposed to human to object, where the power differential is set up so that it appears like I want to “take” something from her.)

Playing a dominant role of authority isn’t the way to go, so be mindful of this in your interaction.

Get Comfortable With Emotions, and practice being vulnerable

Most women I’ve chatted with will quickly bring you in to their “world of emotions.” They talk about how they feel as a way to relate to you. Your job is to share stories of situations where you’ve “felt” a certain way as a way to relate to her. The more you can talk about emotions, how you’re currently feeling, and how you’ve felt in the past, the easier it will be to relate to her.

Does this seem sexist? Well, maybe a little bit. After all, there are plenty of rational, thinking women who don’t want to enter the world of feelings. But I’ve found that having conversations about emotions and showing that you’re not scared of going into this world is the easiest way to build up trust with her.

So there you go. I hope you found this guide useful!

Look, I get it: #metoo has frightened you into thinking that talking to young women is off limits. But if you use these tips, you too can have rewarding professional relationships with younger women. I hope they enrich your world the way they have mine.

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Jon Tesser
Jon Tesser

Written by Jon Tesser

I use data to understand people. I also help early career professionals find career happiness.

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