Online Dating: Putting Your Best Foot Forward from a Personal Stylist’s Perspective

I have recently re-entered the dating world. Oh joy, oh bliss! We all are looking for that elusive connection and a relationship, but first we need to date some “frogs”. I am not a bar hopper and you’re probably not going to meet the kind of man/woman you are looking for at a bar anyways, so I did what any modern woman does and signed up on an online dating site. Eghaaads, the horrors I have beheld! It seems so obvious and logical to me, but from all of the terrible profiles I have seen, here is some FREE advice, from a personal stylist’s perspective, for all of you who want to put your best foot forward on a dating site:



What not to do!

No blurry photos! None. Ever. No bad selfies either for your main photo. No matter what your budget, a good quality headshot that shows your entire face for your main profile picture, is vital. And … smile! I don’t even bother checking out a profile if the guy isn’t smiling. I assume he’s not a happy person and therefore, I don’t want him. People are attracted to smiling faces, not serious or grumpy faces. And, NO sunglasses for your main photo! We need to see your eyes.

Then, add one or two full-length shots so we have an idea of your body type and shape. The photos should be recent … within the last two years. If you have put on some pounds, then take new pictures. This is the most common complaint I hear from men. They ask women out and then the woman shows up 20 pounds heavier than her profile pics. That’s a “no no”, and it you won’t get you very far, even if you have a sparkling personality, because you haven’t been honest right from the start. Someone will like you for who you are now … maybe someone who is also carrying a “few extra pounds”. Be realistic. If you deceive, they will run!

And guys, blurry shots of you off in the distant with your hunting buddies does not cut it. Neither does a distant shot of you in some exotic location in your sunglasses. No photos with sunglasses unless you have some other good photos without them posted.

Oh, and no pictures with your kids or pets. Let’s just showcase you right now. And, no half cut-off pictures where we just KNOW it was your spouse or your last girlfriend! We can see your arm around them … don’t kid yourself!

If you haven’t updated your hairstyle, cosmetics, glasses or wardrobe since your last relationship, it may be time. Outdated glasses turn me off, but I melt for a guy in a suit. Pictures of you wearing a faded, silk-screened T-shirt … really? You can do better than that! And guys, shirtless pics are a “no no”. It’s tacky, period. Don’t do it. “Wife beaters” (tank tops) aren’t great either. And, ladies, keep it classy. Photos showing too much skin will bring you a certain kind of attention, but perhaps not the quality relationship you are actually looking for. I bet the guys would love to see you wearing a form-fitting dress or a pencil skirt and looking like they could take you out somewhere!

If you can’t afford a professional photographer, then get a friend, who is known for taking good pictures, to take some new ones. I promise you, it is worth the effort!


OK, now you have to describe yourself. I know it’s not easy, but it is necessary. Be positive and upbeat. Maybe your online dating experience hasn’t been stellar, but we don’t want to hear about what you don’t want and don’t like. Don’t write an essay, but it should look like you took some effort to describe yourself, what you are looking for, and what your interests are. Be truthful. Don’t sound like someone you want to be. Describe who you are today. Someone will like you just as you are.

If the English language, grammar and spelling are not your strong suit, please get a friend to help you write and edit your profile. Spelling mistakes and bad grammar are a turn-off for me. Maybe not for everyone, but for me, it demonstrates intelligence and care.


If you like someone’s look and their profile, then send them a message and say so. If all you can say is “Hello”, or you send me a “smile”, then how am I supposed to respond? But, if someone messages me and says, “I think you’re attractive and I liked your profile because …”, then I am more apt to check them out and respond.

Next, I highly recommend you ask questions when you are messaging back and forth. When I ask questions and the guy responds, but then does not ask any questions about me, then what? The conversation simply dies. Show interest by asking more questions.

I also suggest you eventually get off “messaging” and try a phone conversation. Maybe you are “ho hum” about their looks, for example, and unsure about meeting up with them. Believe me, you can tell a lot about a person through a conversation … if they have a sense of humour, if they are interesting, if they are positive. You might just change your mind completely about going on a date with them. I recommended this to a friend of mine recently. It totally changed her mind and she now has a fantastic, new boyfriend!


ASK THEM OUT! Jeepers, it’s not a marriage proposal; just a simple “meet up” over a cup of coffee or a glass of wine! If you wait too long and the emailing goes back and forth too long, someone will lose interest and move on. Women want to be pursued! And sometimes guys are too shy or afraid of rejection. So, ask! It may or may not turn into anything, but what have you got to lose … you’re single, right?!?!


In online dating, you have a few seconds to grab someone’s attention … way less time than meeting someone face-to-face for the first time. And you’re being compared to hundreds of others on the same site. So, the morale of this story is that your main profile pic had better be freakin’ fantastic! And then, once you communicate with someone for the first time, you probably only have a day or two to hold their attention, so ask questions and ask them out!

If you are truly serious about meeting someone and dating, pay attention, for heaven’s sake! Don’t sign up or message people when you are too busy to respond quickly. That is the kiss of death. When I don’t hear from someone for a day or two, I assume that they are communicating with others they are more interested in, or simply are not interested anymore. Is that the impression you want to give someone when you have finally gotten their attention? Give online dating some focused time, just like you would any other important project at work or in your life.

Finally, I wish you all the luck with your search! If you have any other suggestions or experiences to share, I would love to hear from you!


Janise Bachler, the Closet Diva, has been helping men and women how to dress and to refine their personal image, or brand, in a way that brings them personal and professional success since 2006. Janise can help you build a wardrobe that works for every facet of your life and that will enhance your success. For more info, visit


Comments are closed.

My newsletter shows you how.