Then Jack Happened


Dear Jack,

I’m asking advice about a friend.  She is in her mid-thirties, like me, but she’s single. She doesn’t want to be single. We talk a lot about her status and the men she’d like to date, but there doesn’t seem to be much of a market for her and she is increasingly frustrated.  She refuses to go on any of the websites I send her, go on a second date or lower her standards, even a smidge, so I am increasingly frustrated about all the talk with no action and now she is getting to the point of saying, “I just want babies and a husband.” She is pretty, successful, nice, family orientated, and refuses to pursue men.  How can I get her to get more aggressive and try and meet more people?

Actions matter more than words when it comes to change.  If a fellow says, “Man I really want to stop partying,” but continues to unapologetically pours whiskey in his coffee every morning, he either can’t change or really doesn’t want to. Until your friend takes some steps, realize that she’s doing what she wants or isn’t currently willing to make strides towards her goals.

That’s not me saying she’s happy single or our alcoholic friend doesn’t want to stop drinking. The first change is most difficult. If she doesn’t follow through with a course of action that she appeared excited about, rather than continuing to ask her about it, change the dialog by saying, “Why didn’t you download the app?” “Why didn’t you go on that blind date I set you up with?” “Why didn’t you call Jack back?”  Get the whys answered and you can deal with the real problem. Maybe she hates dating apps, maybe all she really wants is a baby and not a man, maybe she is really set in her lifestyle and would prefer someone that gives her a lot of space. I don’t know. A goal is easy, setting and following a path is much harder. Once she solves the whys and hows she will be closer to achieving the goals.

I want to say something about asking her to lower her standards. She shouldn’t lower her standards. That’s a recipe for disaster. There is a huge difference between ‘standards,’ which should remain high, and ‘requirements,’ which should be more fluid. She deserves to be with a good person who treats her well. That’s a standard. If she is saying, “I’ll only be with him if he is a gainfully employed advice columnist in his early 20s, washboard abs, with a vacation home,” that’s a requirement. Standards and requirements get confused frequently and it is important that the former remains high while the latter remain flexible. No one is going to be perfect, and if she passes on a guy because he’s a short bartender rather than a tall neurologist, she might be missing out on a great person that meets standards only to end up settling for someone that checks boxes but is not a great person.

Keep helping your friend! Ruts are real tough particularly when you want something badly but things don’t go well right away. You have to start slow, stack good days while overcoming bad ones. She definitely sounds like she needs to cast a wider net. If she stays consistent and sets good habits there’s usually a pay off, but that takes longer, it stinks but that’s the way it is.

Delray you never have to lower your advice columnist standards or requirements, send me your problems at and I promise to write the answer with my washboard abs just banging.