He loves her but another she loves him.

I put on my listening ears and let a brother vent to me. He has a heavy crush on a lovely woman who yo-yos in and out of his life. At the other end he has a different woman who happens to have the dreaded one-way crush on him.

"It's Murphy's Law: I love her and she loves someone else while she loves me and I love someone else."
"I'd say that's more the norm than the exception, Hank."
"It should be simple. Why do I love what I can't have while discarding what I have?"
"Because you're a womanizing mess, and God is punishing you."
"You don't even believe in God."
"True. Your god is punishing you."
"Lovely."
"Let's work on the target of your affection first. Have you professed your love for her?"
"I bought her dinner and sent a text heart."
"A text heart?"
"Less than sign, three."
"Add 'adolescent douche' to the list of reasons why you're single."
"Shut up. Chicks love text messages."
"Whatevs. (That's my attempt to speak your language.) If you don't tell her eye-to-eye how you feel, she could misinterpret your intentions."
"She probably just wants me as a friend and if I open up she'll climb a tree."
"If you love her, she's worth the chase. Now, about your fan."
"Ugh."
"Is she unattractive?"
"No. She's gorgeous."
"What's her issue, other than the fact that she has horrible taste?"
"She seems too desperate for a boyfriend. If I agree to date her, I'll have to watch every step I take because she's so fragile."
"True, fragile toys are stressful to play with. Have you told her you just want to be friends?"
"No, because I might consider taking her on if the woman I love turns me down."
"See? This is why I date my wine glass and ride my bed solo."
"But I like having a girlfriend. I get sex and companionship and don't seem like such a pathetic, lonely turd by sitting at a wine bar night after night getting drunk with empty seats on either side of me."
"None taken, asshat. You'll never be happy with the chick who is chasing you, so shut that shit down. As far as the object of your desire, you had better make your intentions clear before she latches onto another man because you never made a move."
"What if she shuts my shit down?"
"Then you move on to the next love domino, trying to fall for each other."

No Fun Girl

Women tend to overanalyze things when it comes to relationships. It’s understandable because one more Kettle rocks can lead to a candlelit bedroom and the morning-after dash. Still, as a man who has dated a few (hundred) I can say with confidence that couples should concentrate on chemistry and let the rest unfold organically.

There are two types of available women I typically meet. The one brand is in want-to-have-fun mode and isn’t concerned about my 401(k). Usually, this is because she’s in love with another and “taking a break.” She’s less demanding. I dig this chick. Hanging out with her is casual and less like a job interview. The problem is, she typically has buzzing around her an annoying black fly of a friend who is married to her soul mate and pestering the fun girl about her choices.

“Why are you flirting with him?”
“He’s cute. What? It’s harmless fun.”
“It doesn’t make sense. You’re wasting your time.”
“Look, I’m not giving him my ring size or anything.”
“But he’s scaring away other men.”
“It’s just harmless flirting. Relax.”
“He’s too [short/old/fat/broke/married/fashion-oblivious/unavailable/young/bald/etc.] for you to be hanging out with. You need to focus on finding the right man.”

What a cockroach-in-the-salad this “friend” is! She nags the fun girl in hopes of pairing her up so, ironically, she can commiserate with her about bothersome boyfriends. No matter what people invest in, they seek reassurance by persuading others to make a similar investment. Once another teammate is enlisted, they can whine and weep to someone who is no longer in a position to judge.

Another flavor of woman is desperately seeking co-pilot. Yikes! This one dons the doctor smock and begins dissecting the closest man within minutes of meeting him. She gives herself away with her shifting eyes and probing questions. Wise old toads like me know how to answer these questions vaguely.

“So, how much debt are you carrying?”
“Oh, I don’t know. About the same as everyone else.”
“Do you own your home?”
“The bank owns it. I live in it and accumulate cat hair and baubles.”
“How are your books selling?”
“Well enough for me to continue writing. No well enough for me to do so while sunning myself on the Amalfi Coast.”
“Do you think you’ll ever get married again?”
“Holy shit! Did you see that three-pointer Nowitski just hit?”
“I love hiking and bike riding. It’s so beautiful around here. I’m training for a 60-mile ride. You ride bikes, don’t you? How far can you ride?”
“There’s this great new invention called the automobile. You may have heard of it.”
“You seem like a nice guy. Why are you single?”
“I guess I haven’t met the right woman … till now.”

If you’re one of these women, you need to realize the man you’re questioning is gently trying to convert you into the want-to-have-fun woman. If your line of questioning continues without softening, he’ll excuse himself and feed your hatred of players. Be fun, carefree, and casual. Let things play out naturally. Please stop interviewing and start flirting.