How Do You Tell Your Friend She’s Screwing Up Her Love Life Without Ruining the Friendship?

Dear Evan,

My friend is a very pretty, sweet, nice gal. She’s not an Einstein, not particularly into too many hobbies, slightly reserved, and definitely jaded from being on many bad dates. She’s been on and off JDate a million times, (because I try and convince her that her “one” is on there) and continues to go out with “that” guy who says he’s gonna call but never does. Her previous “relationships” have been with guys where they’ve been into her, slept with her, and called it off anywhere from 3 – 6 months thereafter. And as much as she claims she’s “over” them, somehow, they always pop up in conversation and I wonder why she spends her time pining over these retards.

Worse, I don’t have the heart to tell her everything I think she’s doing wrong in her personal life (I know, buy her your book). But in all seriousness, I sincerely wish I could be that fly on the wall and listen to what she talks about on a first date with a guy. I truly believe she talks about shit that most guys don’t care to hear, which inadvertently becomes the kiss of death.

Evan, I need help here. I need to figure out what to say/do for her because I love her very much and really want to see her happy. She is the sister that I never had, yet I feel so wrong for ever offering her any advice. It’s not like I can tell her “Hey – switch up your personality a bit” – can I? I’ve given her hints here and there, but I don’t know how direct I really am. I made her sign up for your blog hoping that she can read and relate to some of the terrible faux pas people make. Do I kindly suggest her to contact you directly? Is that rude? I support your business and all, just don’t wanna step on any toes.

Thank you for reading this mess (if you’ve actually gotten this far). You rock.


Dear Elise,

Thanks for the kind words. And since your friend has no idea that you’re soliciting help on her behalf, I want to thank you for her as well.

Now that we’re done with the niceties, let’s get down to business.

First, an admission of a great mistake on my part. I wrote a book, which, quite seriously, CANNOT BE GIVEN AS A GIFT.

Just listen to the title:

Ready for Lasting Love?
Ready for Lasting Love?

Why You’re Still Single: Things Your Friends Would Tell You If You Promised Not to Get Mad

What a supremely stupid idea. Literally, the only way that this book can be handed to someone else is with the admission that you’ve already read it and found it useful.

Otherwise, it becomes the very blunt tool that the book’s title warns against. Your friends WILL get mad if you give them this book. Especially if they wouldn’t be inclined to pick it up themselves. So how do you help someone who isn’t necessarily looking for help?

Well, let’s parallel this situation with a metaphor.

You notice your friend is looking a little thick around the middle. She’s probably 25 pounds above her ideal weight. Do you:

Only take her to vegan restaurants and hope she picks up the habit?

Hint that you were thinking of taking a power walk every day after work?

Tell her that she might want to consider doing the Atkins diet with you?

Sign her up for a one-year membership at the gym without her permission?

Depending on your level of closeness, and your own gluttony for punishment, you’re going to choice either a, b, or c. Of course, d is the best thing for her. But if I’ve learned one thing as a coach, it’s that I can’t help someone who doesn’t specifically desire my help….

It’s the foundation of every twelve step program: the first step is in admitting that you have a problem. Well, if your friend thinks that the only reasons she’s still single is that guys are shallow, fickle perverts, there is nothing that you can do for her.

Here is a simulated transcript of a conversation I have with new potential clients every month:

Her: I saw an article about you and wanted to see if you could help me with my love life.

Me: Sure thing. Before I get into detail about what I do, could you tell me a little about yourself?

Her: Absolutely. Well, I think I’m quite a catch. I’m 42, I look really good for my age, and I do very well for myself. I’ve traveled around the world, I own my own home, and I’ve had the same girlfriends for over twenty years. I’ve had long term relationships before but in the past five years, I haven’t found anybody that interested me. But since I really want to have a family, I figured I’d call you.

Me: Thanks for sharing. So why do you think things haven’t been working out?

Her: I think that my success can be a bit intimidating. I think most men don’t know how to handle a strong woman. And I think that most of the men I’ve met online have been either liars, losers, or weaklings. Sorry, but it’s true.

Me: Got it. So what can I do for you? I mean, after we’re done working together, the men who date online are still going to be the same liars, losers and weaklings.


Her: I guess. I just figured maybe I could attract different men.

This is where it gets interesting.

Me: That’s true. You can attract different people. But make no mistake about it: the only person we can change is YOU. We can alter how you market yourself, how you act around men, and how you react to different dating situations. But the one thing we can’t change is MEN. And if MEN are the primary reason that things haven’t been working, there’s not much I can do. All we can change is what YOU’RE up to.

There’s usually a short pause, where the potential client digests what I said. And then, generally, she says, “I understand. How do we move forward?”

Then there are those who get upset. They think I’m pointing fingers at them, rather than offering a chance to take control of what we can control, and letting go of the rest.

Such people aren’t calling me for help. They’re calling to get validation. They want me to tell them that the problem is with everybody else, and that nothing needs to change except maybe a new essay on their profile.

In fact, the changes that we need to make are comprehensive. This is why Why You’re Still Single has 29 chapters and only begins to scratch the surface of how we unintentionally sabotage our relationships. As my co-author Linda Holmes wrote:…

“It’s not that you’re single for every reason we’re going to suggest. You’re not picking fights and being jealous and being sexually timid and hanging on to past hurts and hung up on your looks. At least we hope you’re not. But everything you’re going to read about is something we’ve seen — in ourselves, in our friends, in relative strangers, and in all the stories that those people have told us over and over (and over) again. These are observations that hatched over beers, in emails to grieving friends, in pained conversations with people we want to date or are dating or have dated, or, occasionally, in the shower. We’ve done this stuff. We are this stuff.”

So what do you do with a friend, a sister, or a colleague who is running her love life off a cliff? I don’t know. What do you do with a smoker who is headed towards lung cancer? A partier who is due for a D.U.I.? A slacker who will get fired if he keeps showing up late to work?

Really, not much. You can point out the resources available to him/her under the guise of love and concern. But ultimately, people do what they want to do when they want to do it. Sometimes it takes a scary doctor’s appointment. Sometimes it takes a rough breakup. Sometimes it takes a New Year’s resolution. Invariably, it takes a major change of heart — one that embraces, rather than shuns, responsibility for one’s problems.

From what I can ascertain, help can’t be given as a gift. A person has to hit bottom in order to facilitate her own change.

If your friend is open to the possibility that she is the common denominator in not just her successes, but her failures as well, then we can probably have a productive conversation. Please have her call me.

Thanks so much for asking.

If you want more power and control over your own love life, please click here.