How to Find a Date

Maria De La O
9 min readMay 31, 2023

By Judith Gottesman, M.S.W. 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, showing someone how to date is just as important. Some of my clients just hire me for matchmaking and others 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.

I help clients reframe their mindset to make sure they aren’t being too superficial or judgmental about things people say or do. While it’s fine to decide quickly someone is not for you, 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 clients figure out if there’s 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 most important ingredients of a soul mate.

So without further ado …

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

Ask friends if they know anyone (and make it clear you want more than just someone your age who is a warm body). Friends mean well but can often 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 might find each other attractive. So whether this is a new friend or a close one, be sure to share your lists of wants and deal breakers. Ladies, call the men for the first date, and call from a blocked number or a computer-generated one. And don’t give out 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’s 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 web cameras. Moreover, conversation usually flows better on the phone, when not distracted by visuals and worried about how you look on the screen.

When you see a profile you like, here’s how to contact someone. Depending on the site, send a “wink,” a “like,” a canned “flirt.” Or better yet, send a short message saying hello, mentioning some-thing specific you liked about their profile so that they know you read it over and are a real person. Wait a few days and see if they respond. Reply if they do and forget about it if they don’t. Don’t track them and see if they are logging on daily and assume they’re ignoring you. Don’t get invested in a posted profile, especially when you haven’t even heard back from someone, because profiles aren’t people. They are often works of fiction. You don’t even know the person or if you will like them once you speak with them.

Don’t send long form letters, as they are obvious and boring, and so impersonal while pretending to be sincere. They’ll just turn people off. And don’t immediately ask for the person’s name or to contact you off the site. It comes across as pushy and creepy (or super cheap, if you haven’t paid to do more than send flirts or likes, or you’ve posted your email address in the profile). For safety, people (especially women) shouldn’t communicate off the site or give their names or contact info right away, and certainly not in the profile.

Sign up with a matchmaker. There is no substitute for personalized service and the deep knowledge of clients a matchmaker has, which you wouldn’t (and shouldn’t) know about people based on dating site profiles. Also, there is accountability for your date’s behavior since both of you give feedback to your matchmaker. These people are a lot less likely to stand you up for a date, or “ghost” and vanish compared with online daters. 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, and volunteer for nonprofits. Often your friends and family know few people outside of your local orbit, so 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 hikes, or visiting dog parks or dog beaches. If you can’t have a dog, volunteering at the local shelter or for a res-cue group is another good way to make friends and maybe more.

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.

First, a few flirting don’ts:

  • Don’t get overly flirty. Of course, a little is fine — and even good — but there’s a fine line between flirting and sexual harassment. You don’t want to invade someone’s personal space. It can freak them out or, at the very least, turn them off. Along with this comes understanding when to take no for an answer. It’s important to hear them loud and clear, and not dismiss their response if they aren’t reacting positively. Don’t take it personally. You don’t know them, so you don’t know if they’re in a relationship, just getting out of one, not into women or men, sexually traumatized, or just not into you.
  • Don’t be intimidated about making the first move. On that note, don’t go to a place that’s too crowded, you won’t stand out.
  • You go first. Sometimes no matter how hard you try, it’s hard to get somebody to approach you. When all else fails, make the first move. It’s OK, and the other person might be really flattered by the attention.
  • Don’t act distracted. There’s already the basketball game playing on the bar’s widescreen or the impulse to get another beer when socializing. For goodness’ sake, please don’t look around for other prospects while you’re talking to someone. She or he will notice. The kiss of death for a potential love interest is for them to catch your wandering eye. You’ve flirted away and connected with someone, so don’t blow it by checking out others around the room. Focus on talking to the person in front of you, as opposed to wondering who else is there. The grass is rarely greener.
  • Don’t go searching for a pen or piece of paper if you meet someone. One of the best ways to lose an opportunity to get someone’s number or give out yours is to be ill-prepared. Always carry a business card with your number. If you don’t want them to have your last name and number, don’t give out your card. You can ask for theirs. Some people even print business cards with just their first name and a phone number they use only for dating purposes, in order to protect their privacy and stay safe out there. Of course, you can always just put their number in your mobile phone!

Now here are a few flirting do’s:

  • When you’re checking someone out across the room, make direct eye contact. The key to flirting is to look someone in the eye, look away, and then look back at them, so that they know for sure you’re looking at them. Don’t stare! They’ll think you’re creepy. Just catch their eye quickly in a friendly way. Smile.
  • Have a prop. Examples of props could be interesting clothing or accessories. Wear something that invites others to approach you and comment on your look: a sweatshirt with your alma mater, your favorite band, or a funny (but not offensive) saying. Or try out some memorable accessories like a colorful scarf or unusual necklace.
  • Laugh, it’s attractive. Laughter is also contagious. If you’re out with friends, don’t be afraid to show you’re enjoying yourself. If you come across as a fun-loving person, that will suggest you’re someone who likes to enjoy themselves, appreciates friends, and welcomes the opportunity for a good time. You know how to let your hair down, and sharing that zest for life is something you’d love to do with the right person.
  • Look into their eyes. Make it seem like there’s no one and nothing else in the room — like time has stopped for you. Be a good listener. Ask questions. In fact, listen more than you talk. No one likes a loudmouth, especially other big talkers. The truth is most people are delighted to talk about themselves. With a little prodding, most people won’t even notice that you haven’t said a word — not that I advise staying completely silent during their monologue. Pretend you’re a journalist and keep asking questions to keep them going! You might learn something about them, and this back and forth will quickly create a sense of connection, which may lead to something real with time.
  • Do pay attention to your body language. If you’re fidgety, it may help to hold something. Buy a drink, and if you avoid alcohol, hold a glass of sparkling water with lime (it will look like a stiff drink) and keep it in your hand. Remember that if you decide to cross your arms, you’re closing yourself off. When you’re talking to someone, lean in. It shows interest. Don’t get too close though, since you want to respect personal space.
  • Pay them a compliment, make them laugh, or (again) ask a question. Don’t overdo it. The goal is not to embarrass someone or to be insincere, but to make them feel good about themselves. To make someone laugh, you definitely don’t want to say anything that could be construed as offensive. (Remember that humor can be very subjective.) So no dirty joke-telling or sarcasm. Take it from me, asking a question is the most neutral and natural way to go, as long as you don’t get overly personal right away. If you’re in a gym, for example, you can ask how to use a particular weight machine. It is flattering to be asked to share your knowledge, and this can be the equivalent of paying a compliment, because the other person will feel that you consider them worthy of offering instruction.
  • Offer to put your number in their phone. This looks less formal than giving out your business card, like you’re at a work convention. Always volunteer your info first. If you ask for their info, they might give you a fake number if they’re not sure about you yet, or they may feel like you are invading their privacy. If they offer their email address, politely request a phone number instead. Make sure to mention that you wouldn’t want your note to get lost in a pile of email or spam. The idea is to talk and get to know each other, not have a business type interaction through email. And resist the urge to text. Call and TALK.
  • If you get those digits, move quickly to get that date! Use the phone only to arrange it. Try not to talk for hours on end before you’ve had a date. You might think that a long chit-chat session is indicative of a heartfelt connection, but that’s not necessarily true. It might just be that they don’t know how to get off the phone with you, Chatty Cathy! For this reason, plus the danger of oversharing, you need to be aware of the subtle clues: “I really have a lot of work tonight,” “I have to get up early tomorrow,” or other similar statements. It will show that you’re sensitive to the other person’s situation and feelings — another very attractive quality in a potential mate.

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, The Lost Art of Dating author