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Dating Tips For Single Parents: Overcoming the Fears of Repeating Costly Mistakes

By: Mitchell Milch, MSW

For many single parents casual dating is frustrating and annoying. Looking for a new partner, however, can be downright frightening. In fact many single parents who are gun-shy after divorce go in one of two directions. They either convince themselves they are better off not going beyond getting their feet wet at best, or they deny and minimize their fears and make reckless plunges. Why you may ask? Well, the painful realities of divorce that involve children may be likened to having a chronic and debilitating illness like arthritis. Instead of periodic flare-ups of painful inflammation of muscles and joints, we are left dealing with periodic flare-ups of our children’s painful struggles to come to terms with our divorces, flare-ups of our own painful struggles to come to terms with divorce, and episodic painful dealings with our divorced spouses. The evolution and stabilization of split off family units do not come about without mourning obsolete family units and coping with individual and systemic growing pains.

Many divorcees have their self-esteem wounded, experience guilt over making our kids victims of decisions that didn’t work out, and may begin to doubt their abilities to choose appropriate partners. They can even delude themselves into believing they’re entitled to, and can realistically expect, to forge intimate and satisfying relationships without risking disappointments and rejections. Have you endured all the discouragement you can take in one paragraph? Good, now I can resurrect your hopes for a happier outcome the second time around with my dating tips for single parents.

The thematic threat that holds my recommendations together is the adage: "Finding a suitable partner is about racing in slow motion." Like a well-schooled marathoner runner, we are less likely to drop out of the race by virtue of hitting an impenetrable wall of disappointment, frustration and discouragement if we hold back, hold back, and hold back some more despite impulses to fall into infatuation in the early stages of a relationship. Most relationships destined to end when the blooms of infatuation fade are likely to end in the first six months. The faster we move the shorter relationships tend to be, since human beings seldom if ever measure up to our fantasies of them. It takes a history of consistent contacts, continuity of conversations and emotional connecting to build authentic, reliable and sustainable relationships. Rome was not built in a day. Neither are loving relationships.

The marathon doesn’t really begin until after the first half of the race is over, and I contend that most relating doesn’t begin until the flames of infatuation cease to burn in an out of control fashion. It’s at this time that the edge is taken off the urgency to be magnets for each other. We begin to put into focus the outlines of the people we have been pursuing as three dimensional people, as distinct and separate from needs gratifying objects.

What's especially important to consider as attachments deepen are the roles from early childhood your partners might feel compelled to re-live and pressure you to re-live with them. We don’t know someone intimately until we get a flavor of the ghosts of seasons past that we'll inevitably be dealing with from time to time.

I say this no matter how great the chemistry and/or level of comfort between the two of you. If we level with ourselves, we don’t want to get involved with partners who, in their repeating of history, engage in abusive and neglectful dynamics even if they are darlings the rest of the time. Unless, of course, they own these issues as their problems and are actively working them through. I can’t count how many times I have heard inside and outside of my private practice things like: “He was an angel until he moved in, and then became a tyrant.“ Or: “She gave me so much freedom to be myself until we got engaged, and then she wanted to know my whereabouts every hour of the day.” Or: “He was great with my kids until we got married, and then he became jealous and envious to the point of hating them.”

In summary, to ensure that you are not blinded by the uncontaminated fantasies about a potential partner early on in relationships when there is little history together and clear boundaries established, please consider the following recommendations before you make any commitments and go beyond the point of no return:

1) It’s human nature to wish to possess that which holds the potential to satisfy powerful yearnings.

I urge all of you out there to consider staying out of bed as long as is possible and to do your best not to lavish your dates with expressions of infatuation which may be confused by both of you with expressions of love. Infatuations are, by nature, deceptive. The ocean may look very inviting--however, if there is an undertow you simply must refrain from getting in too deep until it subsides. Once you take the sexual plunge it’s hard to swim back towards shore against the tide.

2) We all want to make good impressions with our love interests. It’s incumbent upon all of us to continuously make judgments as to whether our date’s actions are consistent with their words. At the risk of mortally wounding your fantasies, I encourage you to ask clarifying questions, observe responses, and continue to reflect on what’s happ keep in mind ening between you. As you process these interactions with your date is your reality in the same ballpark as his?

3) To whatever degree is possible, keep your dating out of sight of your children. They don’t need to become anxious over what will happen to them should you remarry when you are actually only dating casually. It’s hard enough to make an intelligent and reasonable judgment about selecting a partner without complicating the matter further. And, while you’re going through the initial dating process, keep in mind what kind of stepparent your love interest might be to your kids.

As you reflect on this article I believe you will be much better prepared to avoid major pitfalls as you take the plunge and begin dating the second time around. Good luck!

Click Here to learn more about Mitchell Milch, MSW.

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