Every phone call and convo- no matter how much we asked her not to- she’d start in about Mr.Wrong- hewho told her to take it or leave it. Yup it appears as Mr.Wrong has the most sense about relationships. Finally I unfriended her on FB and deleted her number.

A 50 year old woman whining about a bf for five years? Very tired.
I did my best to fix her advised her to visit this site buy Evan’s books, etc.
She chose to stay stuck. I made my choice.

Please save the comments saying that I’m a fair weather friend.
I believe she was a toxic friend. 

My question, reading your letter, was why are you pushing your friend so hard toward JDate? What about speed dating, or singles parties, or dining out groups, or a mixed bowling league, or a dating or matchmaking service, or synagogue-related groups, or a political group, or woodworking classes, or volunteer organizations, or… etc. etc. etc. What has her luck been like meeting men in the wild?

Any given website should only be “one line in the water.” The fishies are all around us! I know a dating message board where the gals refer to guys they meet via online dating sites as “lobsters”… as having their picture and profile up is like leaving a lobster trap in the water. Every morning, you log on and check for lobsters. Meanwhile, your friend should be getting out there, doing all manner of things both to expand her interests (which in turn will make her a more interesting person), make other friends of both sexes, and incidentally while she’s at it, maybe meet “The One” (although that shouldn’t be her sole focus).

You may SUGGEST all these things to her… once. Twice, tops. But the pushing and nagging in the name of “loving her like a sister” has got to stop, Elise. Why? Because it doesn’t work, as you’ve obviously found. And also because you will risk alienating her.

Evan was partly right when he said the first step of 12-step programs is admitting there’s a problem. Here is the language AA uses:

We admitted we were powerless over alcohol — that our lives had become unmanageable.

Substitute “our best friend’s love life” for “alcohol,” and you’ve got the crux of it. YOU ARE POWERLESS OVER YOUR BEST FRIEND’S LOVE LIFE. You can’t control it, Elise; well, you can BE controlling and pushy and an imperious know-it-all if you like, but that’s your personality flaw, not hers. And if you don’t knock it off or at least find a gentler and more loving and empathetic approach, your lovely friendship is going to become unmanageable. No one likes people telling them what to do all the time when they haven’t asked. After a while, “loving advice” turns into nagging, which can turn into codependency, which will then take you (if you’re lucky) into a 12-step meeting for real to find some serenity again. (The tone of your letter is anything but serene!)

That said, I, too, have single friends who seem to be beating their heads against the wall over the lack of quality men/relationships they’re experiencing. When they are through kvetching, I ask them, “Would you like me to just keep listening or do you want some constructive advice?” When they have felt heard… when THEY open that door… then I can offer my comments and encouragement. Try this sometime and see if you get a better reception. Otherwise, your well-intentioned words will only be so many muffled cries through the solid core, 4-panel oak.

I read your letter and two admonishments immediately sprung to mind: 1) “A girl has to kiss a few frogs before she finds her prince.” and 2) “You have to let your friends make their own mistakes.”

You’re obviously frustrated on behalf of your friend, and that shows you care for her. However, the examples you cite to establish that she’s in dire need of intervention somehow failed to convince me she was a train wreck. You say she’s not brilliant, could use some hobbies, isn’t always the life of the party, and has suffered through a string of poor dating choices that left her scarred. Well, you just described a large percentage
of the adult single female population. In fact, I’d say nearly every female I know, myself and my 90-year old grandma included, would describe her own early dating history as “a string of bad choices”. What better tool for learning to recognize Mr. Right (when he does appear) than plain old trial-and-error?

To be honest, it seemed condescending and vaguely mother hennish of you to even consider saying “switch up your personality”. There’s no one right way to be when out with a man. She could perhaps be a little more relaxed, more positive on dates, but the onus isn’t on her to become somebody completely different in the hopes of attracting a mate. Her job is to be the absolute best of herself so that she will attract the most compatible partner.

Since I seem to be trafficking in old adages today, there’s also this one that springs to mind: “For every pot, there’s a lid.” Perhaps your dearest friend has simply yet to find hers. Compatibility is elusive,
requiring more luck than skill. It can’t be manufactured by anything we DO. A girl can be doing everything right and still all she can do is wait to meet the guy who will respond to her particular charms…who will be equally good for her as well.

In the meantime, if you really want to be supportive, be patient with her. Help her recognize the lessons to be learned from her past dating blunders. Then, focus most of your energies on creating fun times and letting her know she’s important to you. Because in doing so, you will indirectly be giving her the confidence to say no to the next bad-news boy who comes along.