The Lost Art of Dating: How to Get a Date and Turn It Into Something More

Maria De La O
8 min readAug 17


A Jewish Matchmaker’s Step-by-Step Guide to Dating and Finding Lasting Love at Any Age

By Judith Gottesman, MSW with Maria De La O

I’m a matchmaker and dating coach by vocation. While it’s wonderful when I have someone’s soul mate match, the date coaching side of things is just as important. Some of my clients just hire me for matchmaking and some just for date coaching. I find it works best in tandem and my most successful matches have taken my dating advice along the way.

People often blow potential matches by either scaring off someone before or on the first date, or by passing on someone they should have met or seen again, after the first date. It’s common to rule people out before they even meet or on the first date. I help them reframe things to make sure they aren’t being too superficial or judgemental about things people say or do. It’s fine to decide quickly someone is not for you, but you want to make sure it’s for the right reasons. I help them be more open while staying true to their values and goals. And, I help them figure out if they have chemistry. It’s important to be with someone you find attractive.

Otherwise, all you have is a platonic friend. My goal is to help people find their best friend and lover, the ingredients of a soul mate.

What is a dating coach?

Through my coaching, I help people of all ages and relationship backgrounds with varying dating experience, to not only figure out what kind of person they seek, but how to date in ways to make them most successful at finding true love. It’s as if I’m virtually “holding their hand” to guide them through the dating process, from start to finish. Whether they’re new to dating after a long marriage or relationship, or have always been single and just want to change their approach, I am there to provide step-by-step assistance. Many people in their 20s have been busy with school and starting their careers and benefit from my coaching since they don’t have a lot of dating experience. And, often those with extensive dating experience decide it’s time to get objective input from a professional and try some new methods.

There are endless dating sites and new apps popping up all the time, online singles clubs, and traditional singles events and bars. People now tend to text instead of talking on the phone. I’ve even known people to think they are in a serious relationship with someone they’ve never even met! With this ever-changing dating world, it’s good to have some assistance in navigating it. And, partof my job is to be your cheerleader when you get tired, feel disheartened, and may start to lose hope in finding love. Not only do you have to

put in some effort in seeking your soul mate, you have to believe love is out there! n, and ever since I began my business professionally more than ten years ago, people stop me on the street walking my dog or and at parties, in restaurant bathrooms, on airplanes (our conversations usually last the entire flight), at the swimming pool — really anywhere you can imagine. They want to talk about what I do, and see what I think of them if they’re a couple, or find out if I have a match for them if they’re single. No other job I’ve had has evoked such an interested reaction from people. It’s incredible how total strangers share the details of their lives, whether it’s worry about their single adult child, personal dating woes, or the nitty-gritty of their divorces. There are even some rare ones who tell me about their happy marriages.

So is love really about fate? as Jewish theology says? Does a person really need to try so hard, to put in a huge effort to find love? Won’t he or she just find me? , Won’t won’t Won’t I I just stumble upon them at the grocery store, or in a the class I’m taking, or just somehow meet walking down the street?

I get it. Dating can be is tiresome and difficult. That’s why I’m here to help guide and cheerlead for you along the way. And, you know what? Finding a soul mate is about fate, but that doesn’t mean you don’t have to be proactive. Your soul mate is not going to just come knocking at your door while you sit home reading a book or watching TV. Honestly, you do need to make an effort. Just like finding a good job or a good home, you’ll be more likely to succeed if you put in time and effort to do research, hire experts to assist you, and most importantly, expand your search options rather than limit them.

Whether you call it fate, believe in God, or the Universe, or whatever, I think people — when if you they actually make a concerted effort, and they open your their hearts and minds to finding love, and say, “I’m finally ready to be happy and have love in my life and share my life with someone” you’re well on your way — the vast majority of people will find it. It may take time and it may not be easy. Some lucky ones will find love right away and seemingly without much effort. For most, it’s a waiting game, and the timing being unknown and out of everyone’s control, is often the hardest part. People are unique and so will be every experience in the quest for love. The important thing is to get out there, be open to possibilities, stay hopeful, and join the world of dating!

And that’s why people hire me as a matchmaker and dating coach. And that’s why I encourage people to go to events, do online dating, and a variety of other do all those other things to try to meet people, because you just never know when and where and how you’re going to meet your match — and you want to be open and ready when your soul mate they comes along.

So if you’ve ever fantasized that your love would ride in on a white horse and love you forever, please recognize this idea for the fantasy it is. That’s why Jewish tradition has a concept to teach us about God: “God helps those that help themselves.” So get off your tuches!

As we try to teach the children in our lives, we appreciate everything so much more when we work for the things we want. It’s just human nature to not really value what comes too easily to us. I think personally that’s why so many of us look back at “what might have been” relationships that came too easily to us in our younger years.

All of this is to say, if you want a meaningful relationship, you’re going to have to work for it, honey!

But how? After a lifetime, how do you go about dating now? Don’t worry, from the first date through commitment, I’m here to tell you just how to find your own special someone. I’ll use real-life examples from my decades as a dating coach matchmaker to show you the triumphs and the pitfalls the triumphs, the pitfalls, and the pratfalls of some of my clients, so you can go straight to the good, while avoiding the bad. So, get ready, and let’s get started!

How to find a date

Depending on your comfort level and finances, I recommend starting with any and all of the following:

Ask friends if they know anyone (& make it clear you want more than just someone your age who is a warm body. Friends mean well but can often be really bad at matching and just set you up with anyone they know who is around your age, not paying attention to whether you have anything in common or if you may find each other attractive. So, whether this is a new friend or a close one, be sure to share your lists of wants and dealbreakers to give some parameters of the kind of person you’d like to meet. Someone who is appealing to your friend may not be at all for you, so make it clear up front, what type of person is your “type”. And,keep in mind, well-meaning family may want so much for you to be married and not alone or for them to have grandkids, they will suggest settling for anybody.

Pay to be on dating sites.

Choose which to be on based on your values and interests. And, make sure not to join free sites since you want to weed out people who are players and not serious about finding love. Remember anyone can sign up and pretend to be anyone or anywhere. These are impersonal dating sites. Be aware of scammers (with fake or real profiles) looking to swindle unsuspecting members out of money or plane tickets. Sexual predators are also drawn to dating apps for obvious reasons and sexual assaults have greatly increased through them. So, be smart about dating and stay safe. Meet in public places, don’t share rides or give out your address or last name. Ladies, call the men for the first call, and call from a blocked number or a computer generated one. And, don’t give your email address, either. Stick to emailing through the dating site. Be sure to report any strange profiles or uncomfortable interactions you have to the site customer service, and then block that person from seeing your profile and contacting you. I suggest not doing video calls at first since people tend to look bad on webcameras. Moreover, conversation usually flows better on the phone, when not distracted by visuals and worried how you look on the screen.

Sign up with a matchmaker.

There is no substitute for personalized service and the in-depth knowledge of clients a matchmaker has, which you wouldn’t (& shouldn’t) know about people from dating site profiles. And, there is accountabilty for your date’s behavior since both of you give feedback to your matchmaker. They are a lot less likely to stand you up for a date or “ghost” and vanish compared to online dating. If people are willing to spend the time and money to work with a matchmaker, they are likely serious about finding love.

Take classes, join clubs, volunteer for non-profits.

Often your friends and family know few people outside of your local orbit. This is a great way to expand your pool of people. While you learn something new, get in shape, help a good cause, or make a difference in the world, you may just find love along the way!

Adopt a dog.

For all you animal lovers, a dog can be a wonderful way to socialize with people while walking in your neighborhood, going on hike, or at dog parks or dog beaches. If you can’t have a dog, volunteering at the local shelter or for a rescue group is another good way to makes friends and maybe more.

How to catch their eye and keep ’em looking

Whether you are set up with a blind date, meet someone through a dating app, or just see someone who catches your eye from across the room, you’re going to need to know how to flirt.

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