Dating Background Checks: What a Former FBI Agent Wants Singles to Know
09.17.2026

Dating Background Checks: What a Former FBI Agent Wants Singles to Know

You meet someone who seems wonderful. Their career checks out. Their social media looks normal. They tell you they are divorced, financially stable, and exactly who they say they are.

But how much can you actually verify?

At Cinqe, we spend our days making introductions between successful, relationship-minded singles. Safety and privacy are an important part of that process, but there is a misconception about background checks that I think is important to address: there is no single search that can tell you everything about another human being.

I recently sat down with Tom Simon, a retired FBI Special Agent, licensed private investigator, CPA and forensic accountant, to talk specifically about background checks in the context of dating and matchmaking.

Tom spent 26 years as an FBI Special Agent before entering private practice. Today, his investigative work includes background checks, due diligence, financial investigations and fraud cases.

Our conversation reinforced something I have learned throughout my career as a matchmaker: information is valuable, but no database can give someone a guaranteed clean bill of health.

Tom Simon headshot - fbi

What Does a “Clean” Background Check Mean?

This was one of the first things I wanted to ask Tom. If you run a background check on someone and nothing concerning appears, can you confidently say that person has a clean background?

Not exactly.

As Tom explained to me:

“There is no true clean bill of health.”

Professional investigators have access to sophisticated investigative resources that allow them to search information across jurisdictions. But even those resources have limitations.

Tom explained that private investigative databases may match information such as a person’s name, date of birth, addresses and court records to identify possible criminal history.

That can uncover extremely important information. It still isn’t foolproof.

“We are not doing a DNA check on this person,” Tom told me.

That distinction is important for anyone dating, whether you met through a matchmaker, an app, a friend or completely organically.

A background check can provide information. It cannot provide a guarantee.

Man browsing an online dating profile on a smartphone while relaxing at home.

Are Professional Background Checks Different From Online Background Check Websites?

Yes.

There is an enormous difference between entering someone’s name into a consumer people-search website and having an experienced investigator conduct proper due diligence.

According to Tom, a professional investigator can use specialized investigative databases and then examine underlying public records and other sources to develop a more complete picture.

In theory, an individual could conduct portions of this research independently. You could identify every county where someone has lived and search court records in each jurisdiction.

But there is an obvious problem.

A person doesn’t necessarily get arrested where they live.

As Tom pointed out during our conversation, someone could have been arrested while traveling for business in another state. Certain municipalities may also have different levels of digitization and record availability.

That is why he cautions people against assuming any single database represents the entirety of someone’s history.

Can a Background Check Tell You If Someone Is Married?

This was one of the most interesting parts of our conversation.

In matchmaking, people frequently ask some version of: “How do you know he’s actually divorced?”

You might assume there is a national database where an investigator can type someone’s name and immediately see whether that person is legally married.

There isn’t.

“There is no central database in the U.S. of marriages and divorces,” Tom explained.

Instead, an investigator may have to assemble pieces of information and look for patterns.

Is another person with the same last name associated with the residence? Are vehicles registered jointly? Does available information identify a potential spouse? Do property records show that two people previously owned a home together?

Tom told me property records can sometimes provide particularly interesting clues.

For example, records might show that a married couple once owned a property jointly and that one person’s interest was subsequently transferred through a quitclaim deed. That alone doesn’t establish the entire story, but it can become another piece of the investigative puzzle.

In other words, determining whether someone’s relationship history is consistent with what they are telling you can require actual detective work.

What About Someone’s Money?

Dating becomes particularly complicated when significant wealth is involved.

At Cinqe, we work with highly successful individuals, and one thing I make very clear is that a matchmaker is not a forensic accountant.

Someone can tell you that they own a company, have a particular career or live a certain lifestyle. There are things we can reasonably review and questions we can ask. That is different from certifying someone’s net worth.

Tom’s investigative work goes considerably deeper.

He explained that investigators may search for records involving bankruptcies, tax liens, property ownership and other financial or legal information.

He has even had clients ask questions such as: Does this person actually own the house he says he owns? Is he renting? Does he own the car he drives?

Those questions illustrate an important difference between matchmaking vetting and investigative due diligence.

A matchmaker’s job is to facilitate introductions and look for compatibility. A private investigator’s job is to investigate.

Sometimes Old Newspapers Reveal What Databases Don’t

Tom also gave me a tip I hadn’t expected: old newspapers.

He uses historical newspaper archives as an additional investigative resource.

Why?

Because decades ago, local newspapers regularly published police blotters, arrests, court proceedings and community news. Some of that information may not be easily discoverable through a modern Google search.

An old newspaper article might contain information about an incident that never appears prominently in today’s online search results.

It’s a good reminder that Google is not synonymous with due diligence.

What Matchmakers Can and Cannot Verify

This is where I think consumers deserve more transparency from the matchmaking industry.

A matchmaker is not the FBI.

We can interview people. We can ask questions. We can look for inconsistencies. We can establish relationships with our daters and clients. We can use available information and professional resources when appropriate.

But we should never tell someone that another human being has been proven “safe.”

There is no database for character.

There is no search result that tells you whether someone will treat you well six months from now.

And there is no background check that can determine whether two people will have chemistry, share values or build a healthy relationship.

That is why due diligence should be viewed as one layer of dating safety, rather than a substitute for judgment.

What Should You Look for Before Dating Someone?

The lesson I took away from my conversation with Tom wasn’t that everyone needs to hire a private investigator before dinner.

It was that people should understand the difference between verification and assumption.

If something matters to you, ask questions.

Pay attention to whether someone’s story remains consistent over time. Be cautious about major discrepancies involving identity, marital status, employment, finances or personal history.

And when the stakes are particularly high, there are professionals whose entire job is to investigate those questions.

two single people walking away

A Clean Background Check Is Not a Character Reference

This may be the most important takeaway.

Someone can have no criminal record and still be a terrible partner.

Someone can also have something complicated in their history that requires context rather than an immediate conclusion.

Background information is information. What you do with it requires judgment.

As a matchmaker, I want people to pay attention to both facts and behavior.

Does the person’s life make sense?

Do their words and actions align?

Are they consistent?

Do you feel comfortable asking questions?

Are they willing to answer reasonable questions honestly?

Those signals continue long after a background check is completed.

The Bottom Line

Professional background investigations can uncover information that an ordinary internet search may miss. They can identify records and inconsistencies worth understanding.

But even an experienced former FBI agent will tell you that there is no magical button that produces a definitive “safe to date” certificate.

Dating still requires judgment, boundaries, time and common sense.

The goal isn’t to become suspicious of everyone you meet.

It’s to understand what can be verified, what cannot, and when bringing in an expert makes sense.

Tom Simon expert PI detective

About the expert: Tom Simon is a retired FBI Special Agent, licensed private investigator, CPA and forensic accountant and the founder of Simon Worldwide Investigations. He spent 26 years with the FBI and today conducts private investigations, background checks, due diligence and financial fraud investigations. Visit his website here, or connect with him on Instagram @simoninvestigations

Erica Arrechea matchmaker best

About the author: Erica Arrechea is the Founder and CEO of Cinqe Matchmaking, a private matchmaking company working with successful singles throughout the United States and internationally.

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