Dating advice is as old as ancient Rome itself. Ovid, the first-century poet, devoted an entire manual—The Art of Love—to the subject. His guidance was straightforward: wear a clean toga, mind your hygiene, and present yourself well. Other advice, however—such as persistent pursuit or ignoring rejection—would today be more likely to attract police attention than romantic success.

Dating has changed. In Ovid’s time, the principal risk of misjudging romantic interest was an angry rival or a jealous spouse. Today, the consequences can include criminal charges.

In my twenty-seven years practicing criminal law, I have seen a marked increase in cases involving allegations of criminal harassment and sexual assault arising from dating and relationship breakdowns. A significant number involve men who failed to recognize—or refused to accept—that the interest was not mutual. What they understood as persistence, they received as unwanted contact, sometimes resulting in a call from police instructing them to stop.

Other cases move in the opposite direction: there is no follow-up after a first date, and resentment takes its place. Emotions escalate, narratives harden, and the criminal law becomes entangled in what began as a private disappointment.

There are also cases rooted in jealousy and infidelity, where allegations arise in the context of a relationship crisis. In addition, there are cases involving genuine regret—consensual encounters later re-interpreted through shame, peer pressure, or hindsight. Finally, there are cases where age becomes the central issue: situations in which a man honestly but mistakenly believed a young woman was over the age of consent, based on her appearance, conduct, and the setting in which they met—beliefs that, however sincere, require showing you take reasonable steps to ascertain age.

The modern dating landscape is not merely social; it is legal. Misreading interest, consent, or boundaries can carry consequences far beyond an awkward evening. Today, unlike in Ovid’s Rome, getting it wrong may mean explaining yourself not to an offended suitor—but to the police.

Here are six rules in my criminal lawyer guide to modern dating:

1.       Silence Is an Answer

If interest is not reciprocated, stop. No reply, delayed replies, vague deflections, or “I’m really busy right now” are not invitations to persist. In criminal harassment cases, the absence of encouragement is often the most important fact.

From a legal standpoint, once a person knows—or ought reasonably to know—that contact is unwanted, continuing becomes risk, not romance.

Rule: One unanswered message is neutral. Two is risky. Three can be evidence.

2.       Do Not Argue With Rejection

Trying to persuade her that she should like you is not charm; it is a paper trail. Courts do not care that you thought she misunderstood, sincere, or romantic. What matters is how she received the conduct once interest ended.

Rule: Rejection ends the conversation. Full stop.

3.       Keep A Paper Trail (But Don’t Manufacture One)

One clear, calm message setting a boundary, followed by silence, creates the cleanest record. Preserve full conversations if something feels off, but never provoke, bait, over-explain, or write like you’re drafting a legal document. Tone matters as much as content and a paper trail supports credibility—it does not fix bad judgment or replace consent. Never apologize.

However, if you start to think that you should “screen shot” you text messages or keep a photograph “just in case,” then that is your cue to exit.

Rule: Preserve. Do not provoke.

6. Never Chase Closure

“Just wanting to explain,” “just wanting closure,” or “just one last message” are phrases that appear verbatim in criminal harassment disclosure.

Once a relationship or dating interaction ends, continued contact is judged objectively, not emotionally. Your need for closure does not matter.

Rule: Closure is internal. Contact is external. Courts only care about the latter.

7. Consent Is Ongoing — Not a One-Time Voucher

Agreement to one act is not agreement to another. Agreement at one point in the night is not agreement later. Consent can be withdrawn without explanation, apology, or fairness.

Many cases turn on the accused saying: “But earlier she was fine with it.”

Legally, that sentence usually ends badly.

Rule: Every escalation requires fresh, obvious, enthusiastic agreement.

8. Alcohol Does Not Lower the Legal Standard

Alcohol lowers judgment but does not lower the standard for consent.

If someone is intoxicated enough that you are wondering whether they are “too drunk,” you already have your answer.

Rule: If you would be uncomfortable explaining the encounter to a judge the next morning, do not proceed.

9. Age Is Absolute — Assumptions Are Dangerous

Looks can be dangerous. You must show you took reasonable steps to ascertain age. Appearance, maturity, conduct, fake ID, or being in an adult venue often do not help.

Listen to your spider senses.

Rule: If you do not know, then do not proceed.

10.  Pay For The Drink. Let the Waiter Get It.

Save yourself from allegations of drink spiking. Memory gaps often arise where alcohol and hindsight collide. In those situations, she quickly reinterprets her actions as your misconduct. Once that narrative takes hold, it is difficult to dislodge. Keep the bar bill because it shows how many drinks you ordered.

Rule: Do not handle drinks once served. Know the number of drinks consumed.

Following these rules will not prevent you from being charged, but they may prevent you from being convicted.