Get Prepared to Date

Maria De La O
11 min readAug 17


By Judith Gottesman, MSW with Maria De La O

There are many, many ways to get a date. I coach my clients on how to put their best foot forward — whether online or in the real world.

Whether it’s on the date itself or your profile for an internet dating app, you want to really try to present yourself in the best possible light. If you feel that you’d be perfect for somebody, but maybe your self-esteem is a little affected because you were a little hurt from that last breakup, or maybe you feel you’re 10 pounds overweight, or whatever it is: Get out there, do your inner work, start exercising regularly, eat healthy, go see a therapist if you need to discuss your last breakup.

You really want to have a fresh start and you want to feel good. If you’re newly divorced or if you’re back in the dating world after many years away, you do not want to bring this baggage into your dating life. Believe me, I just had a female client I thought would be a great match for a man. Then I got a call from the woman and she told me that the date didn’t even happen. She was calling to report how the date didn’t go. I was really surprised; I thought the two were going to like each other. But on the phone before they even met, she started talking about her ex-husband.
Needless to say, talking about an ex-husband, Needless to say, talking
about an ex-husband, an ex-boyfriend, an ex-wife, and so on is the biggest
no-no you can have if you’re trying to set up a date — whether it’s a first meeting or one further down the road. Of course, you’ll have to discuss past relationships with your beloved when things start getting serious,
but the first few dates are not the time.

App-based dating

As I said, there are many ways to get a date. Some of you are very experienced at app dating, and I coach my clients on how to put your best self out there — whether online or IRL (in real life). Whether it’s on the date itself or on your online profile, you want to present yourself in the best possible light.

Dating can be difficult and a lot of work and effort — and not just for the daters! Since I do personalized matchmaking, I’m meeting with people individually, screening them, doing an in-depth interview for about an hour, and then personalizing everything, tailoring any potential matches to both individual criteria and to my own intuition. This takes into account such immeasurable qualities as the sound of your voice and the look in your eyes, as well as what I consider the most important factors in making a successful match: the sharing of the same values, lifestyle, and goals, as well as a sexual connection. Yes, as a matchmaker, I’m definitely biased in this regard, but online dating is popular partly because it’s anonymous, so there’s no accountability to someone like me. Another reason it’s popular is that it’s so inexpensive compared with a personal matchmaker and takes little effort, since you don’t even have to get out of your jammies to meet a potential match.

Online dating might not typically create lasting relationships, but it does create situations where you can easily meet and date new people. And that’s not to say online dating never works. Happy couples do indeed sometimes meet through dating sites. There are some good people who are serious about finding love on dating sites, along with the not-so-good ones, since it’s popular, cheap, and convenient. My advice:

Be specific and truthful in your online profile.

This includes providing up-to-date photos that show you — not you in a group of friends, at a distance, wearing sunglasses or ski goggles, and so on. Being specific means getting specific about what you seek, but not too specific. You don’t want to miss out on someone just because they don’t check every little box in your list.

Try to meet the person as soon as possible.

Find out if they’re legit and are who they represent themselves to be. Also from a chemistry standpoint, you want to make sure you enjoy the person’s company and are attracted to them.

Don’t be a weirdo.

What I mean is don’t make jokes that could be taken in the wrong way. In fact, try to avoid “jokes” while letting your natural zest for life and humor come to the surface in your profile. It’s a good idea to have your most normal or average friend read over your profile and look at the pictures to judge your attractiveness before you post them. In addition to being “normal,” your friend should be brutally yet lovingly honest. And definitely, no sarcasm.

If you get to the point of sharing your email address with someone after you’ve spoken and met, use just your name, please. Don’t use a “cute” email address; keep it simple using just your name. And please don’t use a Yahoo, Hotmail, or AOL address — you’ll seem hopelessly out of touch.

Don’t use a family email account — I’m thinking specifically of the ones that contain your ex’s or dead spouse’s name.

Yes, I really do have a stubborn client who insists on keeping the dead alive via an email address. I also have some who have their spouse’s voice on their voicemail message.

You never know how, when, or where you’ll meet your match, so you should be open and expand your search options, not limit them.

Simply put, if you do choose to hit dating sites, consider them just one tool in your toolbox. In other words, don’t rely solely on online dating; go to social events, attend events or services at a house of worship, volunteer with a worthy community organization, or otherwise get out of bed and out of the house, looking and smelling your best to be ready to meet new people. And don’t forget to smile!

The profile

These days, it’s a fact that the majority of single people will eventually
log on to a dating site. It’s a quite normal and natural way for people to meet and is more common than using a matchmaker, since it’s much
more affordable — with sites typically charging $20 to $40 per month for membership. A matchmaker is generally $5,000 to $15,000 a year, and
can go up to $200,000. Internet dating is certainly the economical route
if money is a consideration.

I actually encourage my matchmaking clients to also be on dating sites to expand their search options, which is why I provide them profile advice as part of date coaching.

Sometimes the smallest tweak to a dating profile can make all the difference in getting someone to notice you. Follow these guidelines and you’ll have a much better response, and be more likely to attract your kind of person.

The photo
Your photograph is the most important marketing tool you have in internet dating. People sort through dozens, maybe hundreds of profiles, and you need to get their attention so they click on yours. A photo can make or break your chances of getting contacted, so make it a good one. Whether or not you look like a model, everyone can have attractive photos if you keep in mind a few key ingredients:

  1. Make your main photo a headshot.
  2. Have the second photo be a full-length shot to show your physique, no matter how “good” or “bad” it is. You don’t want potential matches to be surprised when they meet you. Remember, for every different body type out there, there’s some-one who likes that body type. Really, there is.
  3. Make sure you have a warm, friendly smile in photos, and show your teeth.
  4. Don’t have other people in your photos. Definitely no photos with exes or photos that look like they have your exes cut out of them! No one needs to see your family, single friends, or coworkers with you. It’s distracting, it can be confusing, and it’s just not helpful in any way. You want prospective dates to focus on you.
  5. Wear clothes that flatter your physique and show it off. Don’t wear sloppy outfits or bulky clothes that make you appear heavier than you are. I see people showing off their winter vacation destinations with photos that show them bundled up in winter sweaters and thick jackets — not sexy! And it makes people look way bigger than they are. Show a little skin, just not too much. Make sure your hair is nice and the colors you wear are bright.
  6. Be sure to look right into the camera. It’s said the eyes are the window to the soul. If you want to connect with someone, people need to see your eyes.
  7. Lastly, if you can’t manage to find a quality photo, then pay for a few professional ones. Photography is an art and a skill. Many people just don’t have the ability to get all the essentials with a friend or family member taking the shots. It’s worth investing a bit for a few really great pictures.

I helped get one client engaged just by telling him to switch out his profile pic. He thought he looked cool, but women wondered why he wasn’t smiling. Men often have this mistaken idea not to smile, and then it looks more like a mug shot. Just by putting him in a friendly pose showing off his beautiful smile and teeth, he was much more approachable. The dates followed.

If you don’t post a photo, you won’t come up in the majority of searches and few people will contact you or reply. A photo really is your most important way to get noticed among the many, many profiles.

The main essay
Keep it short, positive, and light. There’s a sales technique: “Be brief, be bright, be gone.” Think of that phrase as you sell yourself on your profile. You don’t want to share deep, dark secrets or disappointments with total strangers viewing your profile, and it certainly won’t make you attractive to them. Anything you want to say that can be interpreted as negative, just flip it to the positive. If you say you’re sensitive and brought to tears easily, some readers will think you’re an emotional wreck or a neurotic mess. Instead, say something like you’re a caring, loving person. And beware of coded language. For instance, saying you’re looking for a “generous” person is often code for a person who’ll spend a lot of money on you. Similarly, “financially secure” means “rich.”

Don’t talk about your past dating experiences or relationships, or how much time you’ve spent on the dating app. Write only a short paragraph or two. People haven’t even spoken with you yet, and they won’t take the time to read a lengthy autobiography.

Don’t talk about your past dating experiences or relationships, or how much time you’ve spent on the dating app. Write only a short paragraph or two. People haven’t even spoken with you yet, and they won’t take the time to read a lengthy autobiography anyhow. Should you choose to share your life story on the app, remember: Anyone can read your profile. Anyone.

Leave money out of it. You can often guess a person’s financial stability and economic class by other qualities, such as where they live, their profession, and their hobbies, without having to come right out with it. You don’t want to attract shallow, materialistic gold diggers, do you?

Of course, even if you stay positive, you can still go wrong. For example, I had one client — a trim, attractive silver-haired gentleman — who went on and on in his profile about his four kids and 10 grandkids, and how much he loved to spend nearly every waking moment with them. Worse, every single photo in his profile featured him posing with the whole clan. You couldn’t see his enviable physique or his well-put-to-gether outfits for all the children climbing on him!

Needless to say, during his date-coaching session with me, I had to point out the obvious (which wasn’t obvious at all to him): Spend a sentence or two on how much you enjoy being a grandfather — and then get off the subject. Then think of some other activities you enjoy. If you love to take your dog to the park, tell us about it. Use the tools of any good author by being specific and descriptive, and adding a touch of humor (but only if it comes naturally, otherwise your attempts at cornball comedy will only provoke groans on the other side of the computer screen). Share activities you do now or aspire to do with a special someone. Get creative. If you once went to Hawaii and learned to snorkel, talk about how you would love to return to the Big Island and enjoy the fishies with a partner.

In other words, you want to seem available. If you spend all your time with your grandchildren, or on your boat, at work, or at the golf course for that matter, then a potential mate will surmise that you won’t have enough time to spend with them. You also want to make it clear that you are prioritizing the search for romantic love in your life. Finally, you want to convey a fun-loving and sexy persona — vibrant, interesting, and not burdened with a boatload of baggage.

A final note of caution on your essay: This is not the time to be poetic or sarcastic. You may think your artistic license is clever, but others, without context, will most likely find it weird. You may think your sarcasm is funny or clever, but most people will just find it obnoxious. Besides, people reading your profile don’t know you yet, so how will they even know what you write is meant to be sarcastic anyway? They may just think you mean whatever negative or angry thing you just said.

During my college days, I was a psychology research assistant for a study on “dominant and agreeable personalities.” People who were sarcastic were perceived as dominant or aggressive; you want people to see you as agreeable — also known as likable.

Don’t be a liar
No one likes liars. That’s certainly not on the list of adjectives I get when people describe their ideal mate. I want someone dishonest — not what I hear! So don’t lie about your age, or your height, marital status, where you live, or if you have kids. Sure, you may not come up in searches since users set their parameters within so many miles, or for people younger or taller, or whatever. But you’ll be off to a bad start with a potential date if you lie. Honesty really is the best policy. You can search for and contact people, and if they’re ruling you out for any of those reasons, they’re not for you anyway.

Another note on social media, including dating apps that allow you to monitor how many people look at your profile: It may not be good for your state of mind. The fact of the matter is that studies over the years indicate that use of social media tends to be associated with increased social isolation.

If that weren’t enough, in its “Stress in America” report, the American Psychological Association found that being a “constant checker” of social media may increase stress levels. And no one needs that, especially while trying to swim in the dating pool. So limit your searches on dating sites to about once a day, maybe even once a week.

This essay is exerpted from Judith Gottesman, M.S.W.’s The Lost Art of Dating, with Maria De La O. Gottesman is also the owner and founder of Soul Mates Unlimited Matchmaking and My Dating Coach.

Judith Gottesman, MSW