Musings on Life and Love

Image by TheGirlsNY via Flickr

Determined Derek is not the smoothest guy in the world. He tries hard, and he’s persistent. But, as real life often teaches us, effort without skill and persistence without strategy are rarely adequate.

Dawn and Dina are roommates who play on the same flag football team as Derek. One day after a game, Derek decides to ask Dawn out. She accepts, but on their date, Dawn finds that she has absolutely no romantic interest in Derek. Despite the disappointment, Derek remains undaunted.

A few weeks later, after another game, Derek asks Dina out. Although hesitant, Dina decides to give him a chance, as well. Unfortunately, she feels a similar lack of romantic interest as Dawn. Worse yet, she realizes that Derek is saying the exact same lines and taking her to the exact same places as he did with Dawn. When she tells Dawn about her date later that night, Dina notes wryly, “guys gotta know that women talk, so they should probably change up their game if they want to date a girl’s friend.”

In my quest to understand the female mind, few topics have spawned quite the discussion—and disagreement—as the following question that I posed online to a group of friends:

“If a guy asks a girl out and gets turned down, what is the ‘statute of limitations’ for how long he has to wait before he can ask out one of the girl’s friends?”

Expecting one-sentence responses in my inbox, I instead receive multi-paragraph treatises on how guys can be so shallow when hitting on girls and how girls need to stop being so judgmental against the guys who hit on them.

At one end of the spectrum are those who feel that Derek’s behavior is not acceptable under any circumstances. These people believe that as soon as you ask out a girl, all of her friends are immediately off limits. Therefore, hitting on two girls who are friends—what they refer to as “double dipping”—is a strict no-no. As Elana the nurse opines clearly and concisely, “I will go with my visceral response and say, ‘no way.’”

Denice the horse trainer agrees. “There have been times when I am not interested in someone, but I also don’t want him to be interested in someone else.”

Laura the law student defends her position. “If you knew a group of girls, wouldn’t you decide which one you were the most interested in, and hit on her? And if that didn’t work, why would you bother hitting on any of the others? Clearly, she wasn’t your top choice, so you’d just be settling, and that’s never going to work out well in the long run.”

At the other end of the spectrum are those who contend that this attitude is totally unreasonable. As Noel the attorney argues, if a girl expresses that she’s not interested in a guy, the guy should be allowed to ask a friend of hers out immediately. According to Noel, “girls lose all ability to get offended once they 1) deny a guy’s advances or 2) break up with a guy. If they get offended by either, they are trying to reach beyond the grave, and that is just bulls***.”

Taking a more centrist stance, some concur with Noel, but only under certain conditions. As Segal the scientist articulates, “if it’s a casual meeting at a bar, and a guy chats you up, but you realize you have nothing in common, then he starts chatting up your friend, and you realize they have more in common, it may be slightly annoying, but fairly natural.”

Filmmaker Rich agrees, clarifying that openness and honesty are key. “Inevitably, I hit on the wrong girl and discover later that I’ve made a mistake. Now what? I fess up. ‘You’re beautiful, and that’s why I was attracted to you, but our personalities don’t really fit.’ I think it should be fine to make a wrong connection and be able to be honest and mature about the situation.”

Convincing Laura to rescind her previous position, teacher Meg adds, “what matters is that you get to know the second girl before you go after her, and you don’t hit on her simply because she’s the second cutest.”

Entrepreneur Michelle’s story seems to provide the ultimate validation for Rich and Meg’s perspective. At a club one night, she was dancing with a group of girlfriends when they were approached by a guy. This guy clearly wanted to dance with her. As she recalls, though, “I didn’t find this guy’s style anywhere in line with mine, so I turned away and he started dancing with my friend. They hooked up and eventually married!”

Thankfully, Michelle and her friend did not cast the guy off as just another sleazebag. Maybe there’s hope for the double dipper, after all! Then again, if I do choose to double dip, the path I lay for myself is fraught with peril. As I am about to find out, I must tread cautiously….

Margaret the photographer (and coiner of the phrase, “double dipping”) acknowledges that the guy may have to wait a day, a week, or even a year, depending on the specific circumstances, while Deb the medical writer explains that “the length of time depends on the situation, but too quickly can definitely be off-putting to both girls.”

Still, the girls’ reaction to a double dipping will probably be similar every time: slight distaste. After all, as zoo trainer Kelly points out, “the next girl might feel like second best if she knows you tried to hit on her friend first.”

Cindi the graduate student corroborates. “I’ve never met a female who didn’t want to feel like the man she was dating saw her as perfect, and it would be tough to feel that you were perfect if your guy asked out one of your friends, got rejected, and then came to you!”

Here, Amy the law clerk offers some helpful advice. “If the first girl turns you down, you have every right to ask out her friends. That said, try to look like you care a little, and don’t ask her friend out the same night, or maybe even within a few weeks.”

Of course, just when I think I’ve finally figured it all out, Jasmine the theater manager decides to confound the issue. As she admonishes, “women are fickle creatures, and you will never be able to get a straight answer on this one. Because, even though there are rules, we are always changing the rules on you.”

Backing her up, Margaret rolls her virtual eyes and proclaims, “guys really need to stop fishing in the same pond.”

At this point, I feel like I’m back to square one in my understanding of the female mind. But, this is where Rich skillfully reverses the argument and offers his rebuttal: “It works the other way around, too. I was dating a girl once, and I knew it would be short-lived, but it was still more enjoyable than not dating. Anyway, I later discovered that she and my buddy were into each other. My ego was dented, but I could see they were a good fit. So, I told them as much. They’re now dating and having a great time. Does it suck for me? Not really. I helped two people find joy in each other—two people I care about. So, my take is, let go of your ego and recognize the greater good.”

Okay then, between Michelle’s and Rich’s stories, I’m about ready to conclude that double dipping can indeed bring happy results for everyone. So, that brings me back to Determined Derek. After all, I don’t want to make the same mistakes as he did. Noel reassures me that there is nothing inherently wrong with Derek’s behavior. “The guy should do everything within his power to pick up on girls he is interested in. ‘Moving down the line’ may hurt his chances, but that just makes it bad pickup strategy, not morally repugnant behavior.”

Susan the engineer promptly interjects. Although she has no problem with double dippers, she emphasizes that a guy’s sleaze factor, as decided on by the girls, ultimately determines his chances with any of them, and this factor is “directly related to whether the guy is working the ‘volume theory.’”

Unabashed, Abel the financial advisor attempts to refute Susan’s claim. Siding with Noel, he cites his Salesman Strategy. “‘No’ is but an opinion,” he tells me. “Just move on quickly to the next friend. Despite every rational theory as to why it should not work, all of our friends who use this strategy have had phenomenal success rates.”

And with that, Jasmine concedes one glimmer of hope for the guys: “The good news is, if we really like a guy, we throw the rules out the window, friendship be damned.”

So, there it is. The ultimate answer. I can do whatever the heck I want. I can double dip all I need. As long as she likes me, I’m good to go.

Now, how do I get her to like me?