A friend’s old girlfriend is now available. You are attracted to the young lady. Ought you to ask her out?

The Minister of Propaganda and I have dated the same girls without any drama. The Maximum Leader once caused me a wee bit of pain by courting an ex. So there cannot be a simple answer.

The complex answer to this question - a question that, in its import, dwarfs the question of how to put the North Korean nuclear genie back in the bottle - depends on several variables.

To wit:

The first major consideration is how your friend’s relationship ended. If the relationship ended due to misdeeds, one ought to steer clear. If your friend, for instance, cheated on the lass (and why, pray tell, are you friends with a cheater?), than she is bound to have hard feelings. Since you both know the friend in common, your discussion will inevitably turn to that friend and she is likely to express uncomplimentary feelings. This puts you in a hard spot - you can either sympathize with your squeeze or be loyal and charitable to your friend. If the lass cheated on your friend, your friend’s feelings are probably raw and your new relationship will be salt in the wound. Besides, why do you want to go out with a cheater? (Cue the Maximum Leader’s mincing-stepped mockery of Smallholder saying “but this is different! She’ll be loyal to me!” Shut up, Mike. I was 19 for God’s sake!)

If, on the other hand, the relationship ended on good terms - perhaps your friend took a job in another city and they didn’t want to do the long distance thing - you may approach the dating issue with trepidation.

The second major consideration is how serious the relationship was. The potential datability of the young lady is inversely proportional to how deeply your friend cared for her. If the two were married, the answer is, and always must be: Hell no, you may not date her. If the two were engaged, the answer will be the same. If the two dated briefly but never really clicked, you are golden. If the dating was a casual thing among friends, you’re in.

A girl we’ll call Laura really liked the Minister of Propaganda but distance prevented a serious relationship from developing. But she was always excited to see Rob when he was in town. She also enjoyed my company. So when I was in town we’d go out. We all knew this and were fine with it. In fact, another male friend was also in the batting rotation. This was all possible because we were casual rather han serious and there were no hurt feelings on the part of any of the parties. See HERE for more on Laura, or just to have a chuckle at Smallholder’s youthful stupidity.

The third issue, which may or may not be closely aligned with the seriousness of the relationship, is whether your friend harbors any lingering feelings for the girl. If he does, than you ought to steer clear. Even if you think his harboring of feelings is silly. Really. Nothing good can come from ignoring a friend’s feelings.

When I arrived at college, I was fresh from breaking up with the “love of my life.” Love in high school, as my AP European history teacher once explained to a brokenhearted Smallholder, is hell because you have all the emotions to feel love but none of the experience to put it into perspective and none of the maturity to temper the hormones. Going to a meeting of the Baptist Student Union, I met a wonderful young lady. I asked her out within half an hour of talking to her. She agreed, largely because she too was reeling from a breakup (though I like to think my charm and roguish good looks had something to do with it).

We only went out a couple of times. She was a great conversationalist and we had a good time. But I realized that she was still holding the candle for the last boyfriend, who was still in the picture, being a Hamster at Hampden-Sydney just down the road. Rather than risk the pain of really falling for her, I broke it off.

Although we only went out a few times, she was very influential in the humble Smallholder’s road to emotional maturity. She helped me realize that I could start to feel emotional attachment again - something desperately needed since I had responded to the horrible break-up by going out with girls not because I particularly like them but because it was important to have a cute girl on your arm at high school social events, treating dates like accessories rather than people. I’m embarrassed just thinking about it. At any rate, the Baptist girl really helped me get over the emotional hurdle. I still had wistful feelings for her. I’d wonder what would have happened if the other fellow hadn’t still been in the picture.

In fact, I’d often make up excuses just to be with her. Anytime I needed to get around town, I’d call and see if she would give me a ride. I just wanted to spend time talking with her. When she called me out for “using me for my car,” I stupidly did not explain that I still liked her as a friend and was too emotionally stunted to come out and ask to be friends. So I stopped calling. I left the relationship wistful and regretful of my own interpersonal incompetence. She left thinking I was a jerk who had only hung out for a car ride.

Years later, the Maximum Leader briefly courted Baptist girl. Although I did not have any rational basis for annoyance, this bothered me on two levels. First of all, the wistfulness translated into a bit of jealousy, an emotion I’m not used to feeling. Secondly, I was a bit concerned about what she would say about me. (Not that I needed to have worried - she evidently had practically forgotten the blip that was Smallholder - her importance in my life story was not matched by my importance in hers.)

The Maximum Leader and I have a strong friendship and it would have weathered a Mike-Baptist girl relationship had it developed. But I would have felt awkward. So the moral of the story is, don’t put your friend in an awkward position by discounting his lingering feelings. In Mike’s defense, I’m sure he was entirely unaware of my lingering feelings for Baptist girl. College boys don’t often sit around and talk of what might have been with their old girlfriends. He may have been unaware that we had ever dated at all. So this example is for illustrative purposes only - throw no bricks at your supreme generalissamo.

The “hands off!” rule is not absolute. Traversing the same terrain as your friend is fraught with danger, but if the relationship ended well, the relationship was not serious, and your friend has no lingering feelings,you only have one further obstacle in your quest.

Ask your friend. Not because you need permission. Because it is a nice thing to do.

Check out the other members of the Men’s Club: Puffy, the Wizard, and Phin. Or if you would like the ladies’ take on this subject, check out the Divas: Sadie, Kathy, Chrissy, and Silk. Also stop in and visit guest Diva Kelley.