What I Learned in 3 Months from 20 Men and a Matchmaker

Five and a half years after my divorce, I decided to jump into the dating pool for at least three months. Instead of saying no to first dates, I decided to say yes.

Was I crazy? Perhaps.

But I had a lot to learn since I married long before dating apps appeared and had no idea how to use them efficiently. My daughter tried to help, but what works for a college student on Tinder doesn’t work for her mom on Bumble! So I reached out to the experts: my friend, Gina Hendrix, a well-known matchmaker in L.A., police officers from the N.Y.P.D. for safety tips, and of course, all the men below who were a wealth of information.

WHAT I LEARNED

Honesty — Just as you wouldn’t lie on your resume, don’t lie on dating apps. Keep the photos recent. And look your BEST in your profile! Don’t use fuzzy images or be afraid to tell the world how fabulous you are. If you’re a doctor, say it. If you are a professor, share it. Portray yourself accurately on dating apps to attract the people you want to have a relationship with.
Be Mindful of the Sexy Photos — If you can rock the bikini, that’s great…especially if you’re looking for a CrossFit partner. But be mindful about who you’re trying to attract. When Gina redid my dating profile, she removed the overly revealing photos. Instead, she affirmed that you could be just as sexy in a little black dress as in a bathing suit but classier. Who wants to attract the sharks?
Give your actual age. I have heard from both men and women that it’s a turn-off when people lie. One date told me that he scrutinized hands and necks in the photos, assuming that women subtract anywhere from 5 to 10 years from their age. Before our date, he texted me, saying his photos were recent; how about yours? I laughed and responded, of course. But I understood why he asked. One of my previous dates said he was in his mid-50s and turned out to be 71! How can you have a real relationship if you begin with a lie?
Are you really emotionally available? After my divorce, I waited 2 1/2 years before dating again. I needed to grieve and focus on healing. However, I quickly learned that people still in the process of divorce or just emerging from one are not ready to date, let alone share their life with someone. One man told me he never went out with a woman unless she had been divorced for at least a year. I wish I had known that. My first serious relationship after my separation was with a man in a messy divorce who could not be emotionally available, let alone commit.
Be kind. Everyone is at a different chapter in their life. And most people have the best intentions when they come out to date or meet you. So be open to the experience. And if it doesn’t work out, bless them as they leave. Since we all interpret reality according to our experiences, dreams, and imaginations, we never know what another human is truly experiencing unless they share it with us. And that’s ok. Whether they or you know there’s no romantic spark or rapport, say thank you and exit graciously.
Dating apps vary. In other words, Match.com may not be the best app for Boston, or maybe Bumble has few users in Arkansas. See what works and, more importantly, see what type of people sign up for these various apps. Trust me; you’ll know in about 36 hours if something will work for you.
Men outnumber women on the apps. According to a study in 2019, men outnumber women 9:1 on Tinder, and men are 150% more likely to use dating apps than women. So when someone says there are no good men on dating apps, I’m afraid I have to disagree. I’ve met amazing people. They may not have been suitable for me, but most were good decent men. Also, if you’re in an area where there aren’t guys in your age range, widen the geographical circle.
Texting Multiple People on the Dating Apps. I soon learned that everyone was talking, texting, and dating multiple people simultaneously. It made my head spin. But as a process, it exposed what I liked about people immediately. However, do it with grace, and don’t string people along if you don’t feel that spark.
Know your needs. This was hard for me. Growing up in a culture where women deferred to others’ needs, I had to learn what I would or would not tolerate. And it soon became clear while dating. I wanted a real partner, not a project. An honest man who was comfortable with himself, down to earth, and who made me feel safe and respected and could laugh at themselves when they messed up.
Red flags. I think we know most of them already. Inappropriate, vulgar behavior on a date or telephone call. Treating people with disrespect. Not making time for a first date, arriving late without a valid reason, or not showing up at all. Talking over you and interrupting you non-stop. Taking delight in their wrongdoing in their personal or professional life. Sexual promiscuity and bragging about it. Heavy drinking or addictions. Poor relationships with their children. Multiple cell phones. Dismissing your opinions. Talking trash about anyone. Remember, if they say anything in your first interactions or dates that give you pause, ask about it. And if you’re uncomfortable with their answers, remember it’s ok to leave.
Yes, you will be attracted to someone one day. One date told me you had to kiss many frogs to find the right person. I want to add that you have to go on a lot of dates to feel those butterflies again. But they do return. And you will have a rapport and easiness with that person, which makes dating worth it.

SAFETY

Google Voice. Never give out your cell phone number because our phone numbers are personal identifiers attached to most of our accounts. As a result, bad actors can easily access your name, birthdate, address, and family members by typing them into WhitePages.com or TruePeopleSearch.com. If a sophisticated hacker gets it, it can be used to break into your online accounts, including your bank. I learned this from a police officer investigating an identity theft case. After that, I never give my number unless I have to, and certainly not on first dates. Google Voice is an excellent option for a second number and is easy to set up.
Your Photos. If you want to maintain your privacy, do not use photos from your LinkedIn account, social media, newspapers, etc., for your dating profile. Why give away all the information about yourself if you may have only one date with them? I would rather be private and safe.
Google your dates. Vetting dates has saved my friends and me a lot of trouble. However, one girlfriend, a well-known businesswoman, suffered the consequences when she didn’t learn the criminal background of one person. Protect yourself. Use various browsers to find different information. My favorite technique is “Isearchfrom.com,” a Google SEO tool that emulates the Google search location. You have to enter the country where you search from, the language, and the specific device. Then, enter the name or words you’re searching for and click Search. Use it on Chrome, Firefox, DuckDuckGo, and other browsers, and you will see different results.
Matchmakers. Not all matchmakers are equal. Just as you would google a potential date, vet a potential matchmaker. One matchmaker approached me after my separation, hounding me to sign with their agency. I still don’t know how they got my number. After a massive search, I learned that this person had been sued for defrauding clients. Do not assume that any firm, matchmaker or otherwise, is legitimate just because it has a slick website or advertises in Forbes or in-flight magazines. Check everything, including if a company has whitewashed its online reputation. But know, many reputable matchmakers throughout the country truly enjoy connecting people.
Matchmaker clients. Most men who hire matchmakers are looking for lasting, substantial relationships. They are busy entrepreneurs and businessmen who enlist professionals to find their perfect match. However, please beware of the client who lies to their matchmaker or uses their matchmaker as a dating service. If they use the company as a dating service, these men will try to sleep with you as soon as possible and brag about the other women the company sent them. And if a client lies to their matchmaker about their living situation, you’ll find it out within the first date. When the matchmaker calls after the date, let them know if anything was off or shady about the date. This client could seriously damage their business reputation.

*A huge thank you to everyone who shared their experiences with me.

What I Learned in 3 Months from 20 Men and a Matchmaker

5 min