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Oh, What a Tangled Web We Love -- Tips for Online Dating

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By Sexton Executive Security

Published:  March 13, 2007


For better or worse, romance and uncertainty have been bedfellows through the ages.  Some would argue they are inextricably linked; after all, how can anything be truly romantic if everything about it is certain?

One thing is certain: the Internet has opened new forums, methods, and opportunities for people to pursue romance. And those who do look for love on the Web have an entirely new thread of uncertainty to weave into the fabric of their relationships.

Both men and women can reach dozens or even hundreds of romantic prospects by affiliating with one of the many online dating services/publications, or simply by using discussion boards and email to meet and correspond with new people. For many, this can become a wildly addictive pursuit as individuals are freed from some of the “constraints” of face-to-face meetings, which unfortunately can include honesty and forthrightness.

Regardless of how online relationships are initiated, women typically receive more responses than men, and can easily become inundated in a downpour of possibilities. This means a woman could run the risk of not paying close enough attention to those with whom she is corresponding. Put simply, a higher number of responses increases the odds of meeting both suitable and unsuitable partners. So sifting out the unsuitable ones must be given due attention.

A good rule of thumb is to acknowledge and answer certain questions of the heart earlier than one may desire. While the questions may be the same as those that arise in more traditional dating scenarios, the answers may be harder to determine before one’s heart strings have been plucked:

  • Is he single, widowed, or divorced?
  • Have his past relationships been healthy?
  • Is he reasonably responsible personally, professionally, and financially?
  • Are there any glaring moral, ethical, or spiritual disconnects between him and me?


In smaller communities, this information is easily obtainable. In larger cities, it can be challenging but feasible. In the global, veiled community of the Internet, answers don’t come easily.

And while the answer to any one of these questions may not put the kibosh on a courtship, finding out the answer after emotional bonds have formed can be hurtful. And in online dating situations, some of those bonds will likely be formed before a woman feels secure enough to arrange that first face-to-face meeting.

Once in the same place at the same time, the fireworks can begin. And fireworks, while emotionally appealing, can also be very harmful if mishandled.

Any woman who meets one-on-one with a man is placing herself in some degree of emotional and physical risk. Managing that risk can be trickier than some may realize, especially when the two initially met and got to know one another online. Here are some of the harsh realities of online dating that should be sorted through before in-person meetings are arranged:

  • The volume of responses to a woman’s online dating efforts increase her odds of connecting with an unsuitable partner at least as much as with a suitable one.
  • The global, anonymous nature of the Internet makes information about individuals harder to obtain and less reliable.
  • The lack of certain social constraints in online dating makes honesty and forthrightness more difficult to achieve, which can fuel the desire for a face-to-face encounter, especially when emotional bonds have begun forming.
  • The emotional and physical risks of being alone with any person increase when reliable information about that person is less available.


The unfortunate, and generally unspoken, truth about Internet dating is that those who wish to deceive and cheat can have a virtual field day. They have time to develop stories and, by engaging with multiple prospective partners at the same time, they get all the practice they need to become perfect. Innocent people can be lulled into a false sense of security.

Email messages are exchanged, and guards are let down. Comfort levels are established using the Web as a medium, and the desire to eliminate the medium grows.

Now, it needs to be said that many genuine people utilize the Internet to find romantic relationships, and the success stories are accumulating. But as with any potential reward, the risks need to be managed responsibly and people, especially women, need to protect themselves from unscrupulous opportunists.

As a professional investigator who has helped clients discover – sometimes too late – a love interest’s true identity, I encourage reasonable caution. Here’s a road map for more successfully navigating the road to love on the information superhighway:

  • Always keep in mind that the person who has been corresponding with you may be completely different from the person he claims to be. The same is true in traditional dating scenarios, but the truth can be far less apparent with online dating.
  • The Internet has no borders. Respondents may live in cities thousands of miles away or even in different countries. Long-distance relationships, online or otherwise, carry unique challenges.
  • Distance can make adequately verifying a person’s true identity nearly impossible. When someone meets a person over the Internet, she should treat the meeting as though it is in-person.
  • Natural suspicions should be aroused and if something doesn’t “feel right” or “add up” those suspicions should be filed away and re-visited at a later time. If a man sounds elusive about his marital status, for instance, or gives different answers on different occasions, new questions should be asked at an appropriate time and the answers compared.
  • It is common for people to be less than truthful when it comes to appearances. Old photographs can be used to portray a current image. The photo can easily be of someone else altogether. But a woman generally won’t find this out until after she’s committed to the one-on-one encounter.


Appearances are not the most damaging deceptions. My investigation firm was recently hired by a client who had met a person on the Internet and, after a series of electronic exchanges, decided to pursue a romantic relationship. He ignored certain “red flags” and broke general rules of sensibility because his emotions were already entwined by the time they met face-to-face.

The woman never invited him to her home, eventually admitting that, while she was still married, she and her husband were leading separate lives. They continued to meet at his home and, by the time his suspicions were aroused and he decided to seek help from a professional investigator, he was already contemplating “investing” in her business.

By his own admission, the woman told him the things he had wanted to hear and appeared to have been unappreciated and abandoned in previous relationships, so he felt needed by her. He also put his faith in her because of her fairly new car and seemingly lucrative job.

But rather than being a “partner” in the company she wanted him to “invest” in, she turned out to be a low-level support employee. Fortunately, our investigation helped him avoid large financial losses. We were, however, consulted too late to mitigate the emotional damage.

While it may seem like overkill, it is advisable to appropriately check out a person one has met on the Internet if romance is being contemplated. Waiting until emotional bonds are formed impairs one’s judgment.

People don’t think twice about checking the backgrounds of prospective employees, whether there are legal attachments to a piece of real estate for sale, or the history of a pre-owned car. Yet they can neglect to pay the same attention to someone with whom they contemplate spending the rest of their life. But compare the potential damage of a bad employee or suspect car to that of an unscrupulous online suitor. There is really no comparison.

When in doubt, check them out. Online dating services have helped some individuals find their soul mates, and will likely continue to do so. But like any relationship, online dating carries risks. Managing the risks proactively and soberly can limit the pitfalls and help ensure that the uncertainties of romance become nothing more than just another part of the happy ending.

Last modified:  March 13, 2007 - 11:52 AM


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