True Story: I’m An Online Dating Coach For Men

If you've ever online dated or dated men, you've probably thought "online dating coach should be a job." It is! Sara tells us all about what she does and shares relationship tips anyone can use to improve their dating game! >>
If you’ve ever dated or used an online dating service, you’ve probably thought “OMG someone needs to coach these dudes.” Sara does just that! She helps men figure out what they’re looking for in a relationship, write their dating profile, even choose their photos! FASCINATING STUFF.

Tell us a bit about yourself!

Hi there! I’m Sara Sharnoff Chesley. I am addicted to chai tea, puppies, and reality tv.  I live in Charleston, South Carolina with my husband, two rescue dogs, and a baby on the way!

You help men date better through online dating coaching and by auditing their dating profiles. How did you end up in this line of work?

While attending graduate school in Boston, I quickly saw that there was a large singles population and many people were in the city pursuing their academics or professional careers. I learned that many people wanted to find love, but cited that work was taking up the majority of their time and energy.  I knew my single female friends were begging for more high caliber men in the Boston dating pool, so I decided to combine my love for matchmaking, writing, and consulting and launched my online dating coaching business the day after graduation.

What sort of training/education did you go through?

I graduated with a BA in psychology and a minor in gender studies from Indiana University and a Masters of Science in family therapy from the University of Massachusetts Boston. Through my graduate degree I learned how to help people communicate effectively and reach their relational goals. I also worked for a traditional matchmaking company while in graduate school where I learned how to support people on their romantic journeys and find out what leads to successful matches.

Can you describe your typical customer? Who usually hires you?

My clients usually fall into one of two categories-  professional men in their late twenties and early thirties who have never been married, and men in their mid-forties through mid-sixties who are either widowers or divorced and are dipping their toes into the dating world after being absent for quite some time.

What are the most common mistakes that men make when writing their profiles?

The first thing I usually notice is that their profiles aren’t complete! If a man can’t commit to filling out an online dating profile, he probably can’t commit to you!  Many men have a hard time talking about themselves without feeling like they are being fake or conceited.  I spend a lot of time getting to know them well so that I can showcase their personality in a unique and authentic way.

And what are some of the most common dating mistakes?

The most common dating mistake is dating without intention.  What is it that you truly want out of your romantic life? Are you looking for companionship, for casual sex, for a long term commitment? Having clarity around what you need is crucial because otherwise you will date in circles and become frustrated and burnt out by the process.  Having clear goals will make it easy for you to spot a winner and even easier for you to know when to run!

Can you tell us about one of your biggest successes? 

The majority of my clients end up in long-term relationships, and many of them lead to engagements and marriages.  While some dating coaches specialize in men who want to date around casually (nothing wrong with that!) my clients are typically searching for meaningful, long-term commitments.

One of my favorite clients was in his mid-twenties and never had a girlfriend before.  He always felt inferior to his older, more experienced brother and felt that he was destined to be alone.  After a few months of working together, he learned some new dating skills, grew his confidence, and began seeing a wonderful woman. They are now engaged and are currently planning their wedding! It never gets old to hear about wonderful, deserving men finding their life partners.

When you’re editing these dating profiles, do you ever worry that you’re making these men sound TOO appealing and when their dates actually meet them they’ll be confused or disappointed? 

I am always asked, “Aren’t you supporting false advertising?”  Part of my job is getting to know my clients very well so that I can accurately portray them through their profile and by writing introductory messages to women.  The key is focusing on their strengths and really showcasing their best qualities.

Lying or over-embellishing wouldn’t help me or my clients in the long run because the goal is to have a woman fall for my client based on his true character. Also, if I feel that a potential client is dishonest or disrespectful to women, I simply turn him away.  I want to work with men who I would set up with a sister/friend/colleague.

After all your experience helping men date better, what online dating advice would you give women?

My best advice for women who are online dating is to lead with your feminine energy.  I know that this always makes women groan, but this does not mean that you have to abandon your feminist beliefs or act like a damsel in distress; it simply means that you should lead with your softer, gentler side.

Women always say that they want a strong, take-charge, confident man, and that type of energy is seeking a complementary, feminine energy.  If your online dating profile is filled with verbiage about not needing anyone to be happy and not wanting to give up your independence, you aren’t leaving space for a man to approach you.  Your vulnerability, sensuality, and femininity are wonderful assets and I encourage women to embrace them!

Could you give us an example of language that’s a bit more feminine and soft, without being un-feminist?  

Women can show their feminine side in their profiles by describing what fills them with passion while also leaving room for a man to inquire further. For example, “Dancing to the Red Hot Chili Peppers in concert makes my heart pound; it makes me feel so alive! I always look forward to finding the next great show that’s coming to Chicago,” or “I’ve been told that I make the best fudge brownies in town. If you’re lucky, maybe one day you can review them yourself.”

What’s one thing you’ve learned from this that any of us could apply to our daily lives? 

There’s the old saying that you will find love when you stop looking for it.  While I’m thrilled for people who had love fall into their laps,  I really disagree with this mindset.  I believe that finding love can take time, energy, and resources and there is no shame in that.

If you were searching for a new job, you would spend hours on your resume and perusing job listings.  You may even hire professional help to give you an extra edge. Why should finding love be any different? If you are searching for a loving relationship, you should do whatever it takes because I truly believe it is worth it.

Thanks so much for sharing your story, Sara! Do you guys have any questions for her? 

P.S. Not sure if you’re dating ‘The One’? I created a workbook and checklist for you!

photo credit: alex wong // cc

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  1. Leah

    Thanks for the interview! When I was online dating, I always thought a dating coach for guys would be awesome. I helped a few friends set up their profiles. Agreed that many people don’t leave space for someone to engage with them.

  2. Sara Sharnoff Chesley

    Thanks Leah! I think writing your own profile can be really challenging for most people, but it really helps you stand out in a sea full of people!


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