Online dating seems to be both a sign of the times and a necessity. We’ve come a long way. According to a 2025 issue of the Economist magazine:

“Two thousand years ago the Roman poet [Ovid] wrote a manual that promised to explain to his readers the ‘Art of Loving’. Its advice ranged from the sensible (pluck your nose-hair), to the slightly more subtle (brush your teeth, but not in front of each other), to the borderline criminal. When you like a woman, advised Ovid, sit close to her, pretend there is dust on her breast, then brush it off. Which might lead to love but might, today, lead to a lawsuit.”

Dating in today’s world scares me and makes me glad I’m still married, for the rules and methods are so different. In my experience, men and women see dating fromn two different perspectives. Men are not frightened of being attacked, so they seldom seem to consider a woman’s concern. They are mostly just frustrated and annoyed at the endless unsuccessful dates. But women face different issues. Many of them read the rare stories of date rape, attacks, and stalking, and enter the dating pool with various concerns, over and above the normal trepidations.

I must add that statistically, the chance of a mugging, while real, is small according to police records. That part, in my opinion, is magnified out of proportion. However, the risk of creeps and stalkers is very real, but I have not seen any actual data on the subject.

General Advice

When I was an attorney, the advice I gave my clients, I think, is still valid and helpful. Only you can tell what works for YOU and how you are comfortable proceeding.

[1]       Online Data and Pictures Easily Faked. After my mom died, my 85-year-old Dad wanted to date someone age 60, so he claimed he was60. He looked 15 years younger (70) and had me Photoshop his picture so he looked 60. Otherwise, he was approximately accurate. ChatGPT and other AI programs weren’t available so he couldn’t enhance his answer and descriptions. The bottom line is not to rely too much on images and answers; there are maybe a 50-50 chance of being reliable.

[2]       Disclose Dealbreakers. Yeah, something really matters to you, and you are close and ask for information upfront. It doesn’t mean you will always get the truth, but most people will not risk spending time and money on a date that they know will not work out. I have had clients ask me about religion, politics, and children. For the first two, if they are that important, I would disclose them upfront. As for children, in my opinion, that is something you discuss only when you’re serious about a long-term relationship with somebody and not when you’re asking for a first date. I was also asked how I felt about disclosing that someone had cancer or other major diseases, and personally, I suggested that it is not first date material. It is something that needs to be discussed after four or five dates, before you get really serious with someone. But as they say in today’s day and age, “your mileage may vary,” and do whatever is right for you.

[3]       Background Check. Assuming you have a reliable person’s last name, I often asked if you should do a background check. Indeed, in this stage of AI, it takes no more than five minutes and $10 to do a quick background check of any prior divorces, criminal record, and bankruptcies the person may have had. My suggestion has always been to wait until the third date before incurring that expense, but some of my clients did it before the first date.

If you are truly getting serious about someone, I think it’s mandatory in today’s day and age to do a serious background check. I always recommended broaching the subject, as you do one on me and I’ll do one on you. Most people may not be delighted with the idea, but they’re willing to go along. Attorneys see people in trouble, and when a client walks in the door and tells me that their live-in “friend” absconded with their money, I think it is mandatory.

[4]       Face-to-Face Zoom Call. Some people swear by an in-person phone call on the Internet, where you can see the other individual, like Zoom or Facetime. I think it is overkill for a first date. I have no advice either way, as I think it is a personal decision. I had one client who said being asked to do FaceTime was like going for a job interview.

[5]       Where to Go. That is the 24-thousand-dollar question, and everyone is different. I used to take first dates out to a fancy bar (often at a major hotel so we could quietly sit in the lobby). The cost of a few drinks was reasonable, and if we seemed to be hitting it off, then I suggested we go for dinner there. One of my law partners used to meet first dates for coffee (he was cheap and a pessimist), and one of my clients was even more economical and suggested a walk in the park or a visit to a museum. Conversely, others said a good dinner was the price to pay for a first date. The restaurant can tell you a lot. One trendy restaurant in the heart of the San Francisco business district was liked by many, as it was so noisy that you didn’t have to speak much. To me, that is not much of a date; pick an establishment where you can talk. How can you decide if you want to see the other person if you don’t get to know them?

Final Thoughts. Unless you are in college or dating is easy, courting is a challenging adventure with few guarantees. But as the old thing goes, “if you don’t put your pool in the water, you won’t catch any fish.” My one piece of advice is to remember that dating is supposed to be fun, and if you approach it that way, life becomes far more interesting and easier. Good luck.

Online Safety (2)

People only come to an attorney’s office when they have a problem. Even though the issue may arise in only 3 to 10% of dating situations, repeated exposure makes lawyer uncomfortably aware that such conditions can occur. My advice is below, based on experience in training, but that doesn’t mean it is always right for you. Judge accordingly but realize you may be naïve in protecting yourself if you have not yet been “burned.” I suggest the following concepts if you have nothing else to go on.

[1]       Guard Your Privacy. For online dating, when you fill out your application, don’t give any personal information such as your home address, any identifying information, or financial details. There are too many people who troll dating sites looking to scam you rather than meet you. In fact, if someone sounds too good to be true, it might even be a “chatbot,” or fictitious AI construct seeking to gain information about you. Do not use your full name; instead, use a pseudonym (username). When you ultimately meet them, you can give them your real name. Even on the first date, unless you usually feel a strong immediate bond with the person, I would be reluctant to share phone numbers and addresses. Along the same lines, be careful about creating links to other websites or email addresses you use for personal or business information. Those sites might provide enough information to ascertain exactly who you are.

[2]       The Photograph You Use. When you post a photograph, be sure it does not include any identifying buildings or information that can ascertain where you work or live. Also, it’s best to assume that anything you post online might be forwarded to other sites and become public information. Remember, the purpose of a dating site is to hopefully meet someone you might enjoy a pleasant first date with and possibly even lead to future dates. It is not to advertise sex or look for a spouse. That comes later. So, when you put your picture online, depending on your age, you might wish to consider having a photo taken from a distance rather than one that looks especially sexy or handsome. Also, be sure that any pictures you post online do not contain any metadata that can reveal who or where you are. If you don’t recognize the term metadata, do yourself a favor and Google it to learn how to delete such information.

[3]       Don’t Open Attachments. Please avoid opening any attachments or links in an email from someone you only know online. It might be innocent, or it could install spyware or malware on your computer when you click it. When you are seriously dating somebody, that’s another matter. But until you are serious about somebody, I would keep your online communication through the dating website, as it has more protections than most Internet service providers (“ISPs”).

[4]       Choose Reputable Platforms. You don’t want to waste your time, expose yourself, or risk your assets, so I advise using only dating platforms with a strong reputation for strong security and robust profile verification systems. They also use encrypted messages and offer strong, fast customer support. They also respond quickly to detect and eliminate false or fake profiles. On the dating platform, create a strong password, and require two-factor authentication (“2FA”) every time you log in.

[5]       Your First Date. The fifth and final recommendation concerns your meeting place and how to protect yourself on your first date. I recommend choosing somewhere that you feel relatively safe and is public. When you meet them, you should drive or take a taxi or another form of transportation so you can leave at any time without being dependent on anyone else. I would also have a friend know where you are and as much as you know about the person you’re meeting. Then tell your friend to call you and respond using code words at the appointed time. You might say, “I’m with somebody now, can I call you back?” as code for “I’m OK.” Conversely, “I can’t talk now,”” can signal, “Come get me out.”

If you’re meeting at a bar, most bartenders or servers at a restaurant will help you make a quick exit when necessary. Be sure to have some cash on hand so you can pay any bill and leave quickly. I would worry less about hurting somebody’s feelings and more about protecting yourself, even if you err on the side of caution.

Lastly, know how to say, “no.” For women, especially, I have found that a skill that is sometimes a lost art. Google techniques for how to reply, or look for books like mine, Escape: Being Raped or Attacked: Using Common Sense, Karate, and Jiu-Jitsu. Too often, some women say no with mixed messages, which are misunderstood and cause trouble.

A Final Word – Intuition

Your best safety net is your intuition, which Webster’s dictionary defines as the ability to understand or know something immediately, without the need for conscious reasoning. It is also known as a “gut feeling.” The term refers to the human mind’s ability to process information and, almost instantaneously, derive what it considers the correct answer without conscious thought.

The mind sifts through a vast number of prior experiences, minor clues about the current event or situation, and all your past experiences. It concludes so rapidly as to require almost no thought. Your mind reaches the conclusion even when you don’t have all the data you would think you would need to reason through to a conclusion logically. The result is to “trust your gut” or “hunches,” as they are usually correct. If something doesn’t feel right about your date, leave either immediately or early in the date. Something is wrong, and your subconscious recognizes it (even if you don’t want to admit it).

Ted is a retired attorney, so he is writing only as a layperson. This article provides general information only and is not for a particular situation; it should not be construed as advice. It is provided without express or implied warranties of any kind, including but not limited to implied warranties of merchantability or fitness for a particular purpose. If you have a specific problem, seek advice from a CPA, an attorney, a doctor, or other professional. Sorry, my attorneys made me say all that! 

© Ted Gordon 2026

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