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How to Date a Divorced Man: Finding Love in a Complicated Place

Navigating the choppy waters of the dating pool is difficult enough, but in today’s complicated world, people come with more baggage than ever. For women, pursuing romance after a divorce or break-up presents a slew of unexpected challenges. Balancing the demands of children, family, work, and friends requires patience and tenacity, and for many women, finding the perfect mate later in life may seem impossible. When you’re young and carefree, the world is your oyster, and courting someone feels like an anticipated hobby. As time progresses and the responsibilities of life settle in, dating soon proves to be a stressful, downright scary chore. When you finally have the courage and time to begin seriously dating, matchmaking experts remind us that the typical dating “rules” of our youth no longer apply. In particular, if you find yourself thrown into the dating ring in your thirties and beyond, expect to encounter a majority of divorced men.

Leading authorities on modern matchmaking acknowledge that dating a divorced man, even when you are divorced yourself, is a unique, complicated situation. As a smart woman, you need to be prepared to confront a host of obstacles that will try your patience and threaten to end the relationship well before it’s even begun. If you meet a fun, loving, charismatic potential soul mate, don’t be afraid to pursue him. In fact, with the right combination of patience, chemistry, and the appropriate mindset, finding love with a divorced man can be as rewarding as any relationship. Before you fall head over heels, though, realistically consider the following guide to the many challenges that accompany dating a once (or twice!) married man.

His Intentions

Even the most career-oriented, self-sufficient of women might seek a little more than companionship after a divorce or break-up. If you hope to make the ultimate commitment to your partner in the form of marriage, be mindful of his intentions. Expert matchmakers point out that a woman’s expectations going into the relationship need to compare with his, and unfortunately, many divorced men are not so forthright when it comes to what they want. Be forewarned that if the man you’re dating is freshly broken up from his ex, talks about her incessantly, frequently brings up his past marriage, or spends an inordinate amount of time with her, he may not have completely moved on.

Author of Dating the Divorced Man: Sort Through the Baggage to Decide if He’s Right for You, Dr. Christie Hartman insists, “Some divorced men, especially if the divorce is recent, may be more interested in having fun than in having a relationship” (Match.com). Hartman notes that a man’s confusion or indecisiveness about remarriage usually resolves itself after a few years of single life. Before you make a serious emotional investment, be weary of your partner’s behavior and attitude toward the future, and if he’s the right one, give it time. Communicate clearly and often, and in the unfortunate case that he misleads you, move on with confidence.

His Ex-Wife

Perhaps the most liberating aspect of dating a never-married man is the absence of an ex-wife. Many women know that there’s nothing worse than dealing with a partner’s jealous and resentful former spouse. While the Hollywood image of the scorned woman may be exaggerated, there’s no mistaking the complicated role you will play as his new girlfriend. It’s a bitter pill to swallow, but experts always reinforce that an ex-wife, especially the mother of a man’s children, will always exert a certain amount of power and authority over his life. If anything, she will always have a presence, whether it’s in communicating about their brood, arranging visitation, dealing with child support, alimony, etc.  That being said, all relationships with exes don’t have to be contentious. Setting proper expectations and boundaries will help forge a better relationship.

As the new woman, it’s important to maintain a cordial rapport with her to ensure the harmonious relationship of everyone involved–especially for the children. This can be endlessly frustrating, and more times than not, you will lose out on his time and attention when responsibility calls.

His Children

In the 1970s, television classic The Brady Bunch set forth a long-lasting, impractical, downright ridiculous expectation for blended families. When you, the man you are dating, or both have children from previous relationships, the romance itself often takes a backseat to the complicated demands of satisfying your offspring’s needs. On the contrary, many women who have no children find themselves surprised at how much time and attention children can require, and they soon realize they are unwilling to sacrifice their freedom–and alone time with their new beau for his kids. When expert matchmakers evaluate a potential couple’s compatibility, the issue of children can play a key role in a relationship’s future success. If you find yourself falling for a divorced man with children, whether young or old, take a pragmatic approach to their demands. While a never-married man is meeting buddies at the bar, taking vacations, and is otherwise living a life of pure, unadulterated freedom, a father’s world tends to be dictated by his children. For some women, especially those with kids, this is a way of life too, but a complication no less.

His Money

Although everyone knows the word “money” should have no place in the same sentence as love, the modern woman is savvy when it comes to her financial reality. When you are older, established, and are pursuing romance with a financially settled man, the topic of divorce throws a wrench into the equation. Along with his ex-wife and children, a divorced man can deliver up baggage in the form of required alimony payments, child support payments, and perhaps other personal debt unrelated to the divorce. If his family stayed in their original home, then he may have a mortgage–or two–and a number of other expenses that support his former family. All of these monetary responsibilities complicate your future together, take away from your partner’s immediate ability to spend, and generally breed awkwardness and resentment in new couples. Be careful in assessing a divorced man’s financial liability, and if you choose to look the other way, prepare to make it your own.

Pursuing a relationship with a once-married man can seem daunting, but when love takes its inescapable hold, women shouldn’t shy away from a potentially fulfilling, loving union. Modern dating can be complex for a variety of reasons, and with American divorce rates sky-high, men with little to no baggage are difficult to come by. After all, aren’t we all complicated?

If you are in need of advice regarding your relationship with a divorced man, or if you need assistance in finding your true love, contact an expert at LunchDates Professional Matchmaking.

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