UPDATE: Should I spy on my son's mysterious new girlfriend?

11/15/17 01:47 PM EST

By Quentin Fottrell, MarketWatch

This father fears his wealth will fall into the wrong hands

Dear Quentin,

Our only child has begun his first serious relationship. He is in his mid-20s. He has a steady career, money in the bank, no loans or debt where not much will hold him back from a rapid progression from dating to married. We are not 1% wealthy, but through some calculated risk taking, incredibly hard work, good money and asset management, my wife and I have managed to set up a very comfortable future. Money isn't everything, but it sure makes things a heck of a lot easier.

We are not helicopter parents, but we have sought to instill in him our drive, work ethic, and attention to detail that has served us well. We have tried, and think we have succeeded (on most days) to develop this internal compass that will serve him throughout his life. All in all, he is well adjusted and squared away, not to mention we both have an enviable relationship with him and want him to find someone who will be his partner in life.

While this is not a broad brushed condemnation for all millennial women, my wife and I are terrified of a person that may take advantage of our son and his situation.

Read:My dad didn't love me! He only left me $10,000 (http://www.marketwatch.com/story/my-dad-didnt-love-me-i-barely-got-mentioned-in-his-will-2016-01-31)

Which brings me to the dilemma: His current girlfriend has some gaps in her history and has exhibited behavior that points to a pattern of underachievement. Suffice to say that she has suddenly and significantly dialed back current employment and long-shot career plans since my son has arrived on the scene. Additionally, there has been some evidence of police activity at her residence. What kind of activity, we don't know, but the total package scares us.

We have the means to dig deeper into this young women's past, and feel guilty going "full recon", but we want to protect our son (and our combined assets). Yes, at all costs. And, no, we haven't figured out yet what to do with any uncovered negative information, but I think we could figure something out if it protects him from potential disaster. Sure, our son is entitled to make his own life, and work through his own mistakes, but it would kill us if he/we were taken for a ride. No matter how old he gets, he is still our son. This is where we are stuck as we watch this relationship progress.

Thanks by the way, for publishing some of the most gut wrenching stories of the very personal lives of your readers.

Ed in Boston

Dear Ed,

The government (http://www.marketwatch.com/story/4-ways-to-be-invisible-online-1329502910909) is spying on us. (http://www.marketwatch.com/story/4-ways-to-be-invisible-online-1329502910909)Our employers (http://www.marketwatch.com/story/whos-a-bigger-snoop-the-nsa-or-your-boss-2013-06-10) are spying on us. Our spouses (http://www.marketwatch.com/story/5-apps-for-spying-on-your-spouse-2014-03-10) are spying on us. It was only a matter of time before our prospective in-laws joined the club.

If you would like to continue to have an enviable relationship with your son, one many parents across the land would want with their own children, I would suggest treading very carefully before hiring a private investigator to look into this woman's past. I once interviewed a P.I. in San Francisco and she told me: "We go over, shake the tree and see what kind of monkey falls out (http://www.marketwatch.com/story/employer-spying-shrieks-in-france-shrugs-in-us-2013-12-17)." Boy, she had a lot of moxy. But from your son's point of view, digging up dirt on his girlfriend based on second-hand gossip may reveal more about you than the woman in his life.

You say you are scared that someone will take advantage of your son. I caution you to make sure that this fear doesn't lead you to find problems where there are none. Stories of "police activity" at her place sound so vague and spurious that I would consider the source and, if you must, ask your son face-to-face with as much incredulousness as you can muster. Not everyone he meets will be on the fast-track to making partner at their law firm and if his next girlfriend is European royalty or American heiress, she will probably have skeletons in her closet, too.

Don't miss:10 things married couples won't tell you (http://www.marketwatch.com/story/10-things-married-couples-wont-tell-you-2014-10-31)

Take a lesson out of a previous letter to the Moneyist. This father threatened to disinherit (http://www.marketwatch.com/story/i-will-disinherit-my-daughter-if-she-marries-this-man-2015-12-14) his daughter if she married a man he described as "controlling, manipulative, repulsive, a coward and a thief." He wrote, "I don't want any part of my estate to go to, or be in control of, this coward and thief she wants to marry." I said he too was controlling. After my response, he wrote back (http://www.marketwatch.com/story/two-controlling-fathers-unhappy-with-their-children-speak-out-2015-12-18) to say he didn't want to lose his daughter and would step back and allow her to make her own decisions. "Reading it again I see the rage coming through my words," he said.

Allow the apron strings snap and allow your son to navigate his first real relationship as the man that you have raised. This is his first serious relationship. It won't be his last.

Do you have questions about inheritance, tipping, weddings, family feuds, friends or any tricky issues relating to manners and money? Send them to MarketWatch's Moneyist (mailto:qfottrell@marketwatch.com) and please include the state where you live (no full names will be used).

Would you like to sign up to an email alert when a new Moneyist column has been published? If so, click on this link (http://www.marketwatch.com/tools/alerts/newsColumn.asp).

-Quentin Fottrell; 415-439-6400; AskNewswires@dowjones.com

RELATED: I give my son money and his wife gives it to her church (http://www.marketwatch.com/story/i-give-my-son-money-and-his-wife-gives-it-to-her-church-2015-08-21)

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(END) Dow Jones Newswires

11-15-17 1347ET

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