How To Date A Divorced Guy, And Why It’s Worthwhile

An appropriately blurry photo, taken long before my divorced boyfriend and I came out as a couple.
An appropriately blurry photo, taken long before my divorced boyfriend and I came out as a couple.

Divorce is a doozy of a word. To most, it connotes failure, neglect, philandering, physical and/or emotional abuse, irreconcilable differences, the division of assets and toxic custody disputes.

It’s no wonder so many cringe at the idea of dating someone with an ex-wife. He must so be damaged! He must have so much baggage! He must have an incurable case of halitosis! 

But for the single gal interested in finding Mr. Right, disregarding the divorced set isn’t just silly — it’s downright inefficient. According to the National Survey for Family Growth (NSFG), the chances that a separation from a first marriage transitions to divorce is 53% within one year for women ages 15-44, and 86% within five years. What that translates into is a vast pool of people with priors in the Marriage Department. To overlook this group, then, is to reduce one’s options by a significant margin.

Perhaps you want to be the only woman whose veil her husband removes for a special nuptial smooch; the only one to whom he gives a shiny rock on which he spent at least three months of salary; the only one whom he calls “gooey pie sweetheart” because your love is the sticky, finger-licking-good-to-a-sickening-degree kind. If only Happy Endings weren’t more likely to involve a wink, a nod, and a handjob than the Disney movie crap we were raised on.

I’m not suggesting that anyone give up on happiness — just that we broaden our idea of who or what might lead us there. As someone who’s been dating a divorcé for some time now, I can assure you there are benefits to landing a man who’s signed a few more legal documents than the next guy.

First, the divorced have a proven track record of commitment. If your goal is to enter into a serious relationship, it should reassure you to know that a man doesn’t suffer from whatever phobia plagues perpetual bachelors. Second, a divorced man has likely learned from his past relationship mistakes. What some call baggage, others call vital experience. Lastly, if your plan is to marry, the statistics are on the divorced dater’s side. The NSFG cites a mere 10% chance of separation from a second marriage ending in divorce within year one!

For all the perks that come with dating the divorced, there are, of course, specific complications to consider. But to help those interested in tapping into this underrated category of eligible men, I’ve outlined the following five-point survival guide.

1. Be Good At Sex.

It may be difficult to pinpoint what causes a marriage to crumble, but I think we can agree that one thing is generally true of troubled couples: They do not have a lot of good sex, at least not within their matrimonial union. Unless he was completely cavalier about seeking sex outside of marriage, your divorced boyfriend has likely experienced a period of sexual deprivation in the not-so-distant past.

What I’m getting at is that he will be duly grateful if you’re a badass in bed. Most men appreciate a woman who knows what she’s doing in the sack, but the divorced ilk are positioned to be doubly grateful for your bedroom enthusiasm. Being good at sex doesn’t have to mean mastering acrobatic tricks or being overly generous with fellatio, but it can. I, for one, recommend a class at Babeland called The Art of the Blowjob. Especially when dating divorced, the effort won’t go unappreciated.

2. Don’t Disparage His Ex

If you have to vent about your divorced boyfriend’s ex, call a friend. Whatever you do, avoid berating her in front of him. Anger and resentment are unattractive emotions, and you do yourself no favors by coming across as bitter.

By speaking ill of his ex, you also risk triggering his defense mechanism. No matter how many times he wonders what the fuck he was thinking when marrying the psychobitch, he was indeed married to said psychobitch at one point. This suggests that there’s a modicum of warmth towards her resting somewhere deep beneath his prostate, and it’s not in your interest to set it free by attacking her. Let him disparage her, but don’t get sucked into that vortex.

a.) Don’t Be Creeped Out By Your Resemblance To Her

Since it’s unlikely that your divorced boyfriend’s taste in women has changed all that dramatically following his first marriage, chances are that you’ll resemble her a bit physically. That might make it tricky to insult her appearance (internally only, of course), but it’s something you have come to terms with.

b.) Refrain From Googling Her

Google stalking is standard practice these days. However, it’s dangerous to indulge your click-happy fingers when it comes to your boyfriend’s ex-wife. Depending upon how widespread her web presence, Googling the ex can lead to fixation over who she is, what she’s doing and who she’s hanging out with. It can also lead to discovery of the dated New York Timeswedding announcement you don’t want to read, and reread. The main risk is that you end up uttering those disparaging thoughts you’re meant to suppress. Choose a celebrity to obsess over instead.

3. Forget About Finances

They say divorce is expensive because it’s worth it. Without a doubt, financial issues are a leading cause of divorce. That’s probably because money matters, and money matters suck. If you’re interested in dating a divorcé, you absolutely must accept the fact that his financial commitments to his previous life will be ongoing.

Your divorced boyfriend’s alimony and/or child support payments will detract from your disposable income as a couple, and drain the funds that should be saved to support your hypothetical future family. Deal with it. If you can’t look past the cost of his first marriage, you probably deserve to be in a vapid relationship with someone who earns stupid amounts of money, but sucks in bed. Try Wall Street.

4. Be Discreet

Your boyfriend divorced his first wife, but not his entire former life. It is thus bound to be somewhat awkward for him to integrate you into his social circle, and you should be mindful of this. If he prefers to remain discreet for a while, respect his choice of hole-in-the-wall restaurant and his hesitance to be overly affectionate in public. He might ask that you refrain from advertising your relationship via social media channels, too. If you like the guy enough, it should be sufficient to be together without the whole world knowing about it from the start. On the upside of forsaking your Facebook relationship status, by being so cooperative and understanding you will showcase your unwavering devotion.

5. Be Patient

A person who’s been-there-done-that in the marriage sphere will probably be hesitant to launch full throttle into his next relationship. In short, expect milestones to arrive at a more sluggish pace. Yes, it will be frustrating to meet his parents and to cohabitate much later than you’d like, but his reluctance to move quickly is not a reflection of his lack of feelings for you.

Fielding questions from prodding family members isn’t fun for anyone, and the questions posed of a divorcé are roughly one thousand times more needling. Through divorce, after all, one relinquishes their I Know How to Pick Them benefit of the doubt. Try to view the man’s plodding approach as a move to protect you from dubious glances across the honey glazed ham at Christmas.

When it comes to checking off the all-important Signs of Commitment — from the magical appearance of a second toothbrush at his house to the invitation to join his family cell phone plan — pad your timeframe, just not so much that you feel you’re compromising your self-respect.

Whether or not “amicable divorce” is an oxymoron, marital breakups transpire each year, leaving a trail of suitable single people in their wake. I would encourage everyone to abandon whatever hang-ups they might have about finding an “I Do” virgin — not only because it’s mathematically advantageous, but also because dating divorced has its own rewards. Remember, you’re not sloppy seconds. You’re an upgrade. TC mark

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