Introduction: The following letter comments on a friend’s experience with a woman who cancelled a date because of an emergency yoga session popping up. He’s a Catholic in his late 20s looking to find a woman he can marry. I share this letter because I find his situation instructive. I freely admit that my advice does not reflect conventional wisdom on dating, but it may resonate with those in the same boat as my friend. I slyly replaced the real names with those of the characters from Shakespeare.


I’ve already sent a string of lengthy texts expressing what I thought when hearing about your date. Still, after mulling over it a little more, I become increasingly annoyed. She likes the attention you’re giving her, but she doesn’t feel the need to reciprocate or be affectionate, so I’m almost positive she hopes to put you in the friend-zone.

From what I can tell, it’s clear she has formed an unromantic opinion of you: nice guy, pretty smart, and kinda nerdy in an endearing sort of way, BUT also a weird religious guy who craves good sober fun, mature relational commitment, and serious conversations; looks-wise, he’s handsome, but in a wholesome manly kind a way, not in the familiar boyish one. I wouldn’t say this is an inaccurate judgment, but I think it’s something that scares her. She probably wants something noncommittal, undefined, and “fun” –in other words, something that makes her feel younger.

She seems rather full of herself and lives in a closed-off echo chamber that continually strokes her ego in graduate school. She’s obviously not ready to face the real world, which you probably represent with your “job,” your “books,” your “maturity,” your “faith,” and your “courtship.” Like many millennial women approaching or hitting 30, she think she has plenty of time and that spinsterhood, dead-end hookups, or settling for mediocre beta men are impossible outcomes for a woman like herself.

From what you told us, it sounds like she panicked (“Oh crap! This guy really likes me and wants to have something serious! He’s like Catholic or something! Erg! How do I get out of this?! Ah, I know! Yoga!”). We’ll see if you get to see her again. She may want a free meal, more compliments, and a comfortable evening of establishing a hazy friend-zone.

Anyway, that’s how I’m seeing it, and it bothers me because I think she’s missing out and being stupid. Here she is, a girl who’s on the older side, with a massive amount of debt, with no serious prospects, no real depth of character, still living the student life. Sure, she’s pretty, in shape, and not totally boring (I would hope, getting her doctorate in performance!), but she’s kidding herself if she thinks she can play games with quality guys like yourself. This sounds a little too much like Juliet, who’d be more content being a girly-girl dating her man-child than having something real with a real guy who could make her so much happier.

Even these knights would agree.

Even these knights would agree.

So where does that leave you? Was this all a waste of time? Are you being rejected because there’s something wrong with you? I sincerely hope you’re not thinking that. I think this was a good experience, and one that should lead to greater willingness to date and have a romantic relationship with others. I think you’re probably learning that being the gallant gentleman willing to give the girl the benefit of the doubt does not exactly pay dividends in the love department.

As I’ve said, it’s key to recognize your own worth and help these girls recognize their relatively deficient worth (what I call, “taking the person down a peg”). Consider: the girls whom you actually court, like Portia or Juliet, take your attention for granted; the girls whom you occasionally hang out with, like Desdemona or Cordelia, seem to draw closer to you. Why the different response? It’s not simply that “Nice guys finish last” and “Girls like jerks,” but that you put the former pair on a pedestal and took the latter pair down a few notches.

Just think about your meet-up with Desdemona–which you had much more to talk about, by the way, than your actual date with Portia. I have no doubt that you probably took her down a few pegs without even thinking about it. By this, I mean that you probably just asked her questions about mistakes she’s made, the place that she works, the place where she lives, and the dreams she apparently has. When she talks with you, she is reminded of her immaturity, her relative inexperience, and her inadequacies. This, in turn, makes her want to prove herself to you and get your approval. That’s why she probably wants a real relationship with a real man, not some girly man stuck in college. Even though she’s inexperienced and self-absorbed, she wants to be taken seriously and do respectable things. Cordelia is probably the same way.

It’s also important to remember that all these girls think they’re hot stuff. This is just the default position of relatively attractive women in their 20s. The culture puffs them up, and they lose their sense of reality. Even if it conflicts with your desire to be a gentleman, your job as a single man looking for a soulmate is to break down this conceitedness. Not by cutting them down and being a jerk, but by using a kind of socratic method that delicately deconstructs these vain notions through honest analysis.  I think the girls who cooperate prove that they’re worth your time and that you can build something solid with them. The ones who hate this and make excuses can join the growing ranks of desperate single women their 30s and 40s crowding the dating websites.

All this reminds me so many “love” sonnets where the poet basically says that the girl is getting old so she better get over herself and be with him. I’d look at these and chuckle, thinking, “Man, what a pig!” Now, I tend to think of it as an elegant way of stating a profound truth about romantic love (eros): We are creatures with limited time on this earth, so we should stop pretending otherwise and recognize a good thing when we see it. Gather ye rosebuds while ye may, indeed!

375026 02: The cast of "Sex And The City," Season 2 Clockwise from top left: Cynthia Nixon, Kristin Davis, Sarah Jessica Parker and Kim Cattrall. 1999 Paramount Pictures

And that’s why Sex in the City can only happen on television.