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

Two mature women having a conversation

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:

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.

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  1. 1
    mrs. vee

    Elise –

    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.

  2. 2

    Hi, Elise. I like Mrs. Vee’s advice about encouraging your friend to be her best self so that she will attract a compatible partner. True love is when two flawed people get together and consistently bring out the best in each other; or putting it another way, we all have baggage, so the trick is finding someone whose baggage is compatible with yours.

    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.

  3. 3
    Flower White

    I have just cut off a female friend who, for the last five-FIVE years has used us, her friends, as a springboard to complain about her  dysfunctional  relationship how she had a bad boyfriend and was screwing up her love life

    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.  

    1. 3.1

      There are toxic friends out there.   Sometimes, their “problems” somehow become their life and encroach on your life and positive energy.   I had a friend like that.   Wonderful friend at the   start. Then she became a major complainer.   She drudged up stuff to have something to talk about.   She wouldn’t move one.   She wanted to be unhappy.   Me, I love being chipper! She hated when I found a guy I loved.   Got right in the middle to stop it.   Yes, he was not my Prince Charming, but it was crappy of her (she laughed in my face). Sometimes, you have to break-up with friends like a romantic interest.

      I have a brutally honest friend named Kim.   I ask her for advice and she is totally honest.   Her husband knows this but also knows that I would rather hear the truth than be lied to.   She is like another sister to me.    He is also a friend of mine and both want me to be happy and offer great guy advice on the spot.   And, I take it.   Even when it’s out of my comfort zone.

      If your friend and you (OP) are really and truly that close, ask her why she thinks things don’t work out with these guys.   Ask if there’s a point where things change.   Is it a particular point in the relationship?   Is it after sex?   Does she talk about wanting to be a mom all the time?   Does she do all the talking? As her friend, if she is asking, you should be honest.   Not to the point of making her cry, but honest.   Lying to her isn’t going to help her.    I would rather someone give me advice that will make my life better, than lying to make me feel better for five minutes.   If she doesn’t want help though, that’s her choice.

  4. 4

    It’s hard when you care about someone and you can see their errors, and all you want to do is give them a good shake and talking too! In the past I have had a few situations where I wanted to tell a friend something so she could make improvements and get a better result. The way I did it was by saying that I used to have x problem and I did x to resolve it, have you ever been in that situation? And of course it all depends on how the conversation evolves from that point. Fortunately the penny dropped for my friend – good luck! But the key point that Evan makes – if the person is not willing to acknowledge that she may be the one with the problem, then all the help in the world is going to full on deaf ears.

  5. 5

    1. The insult “retard” meaning stupid came about as a way to mock the mentally retarded, as intellectual disabilities were once called. It doesn’t matter if the technical definition means “slow,” it is a cruel term and it needs to go.

    2. You don’t sound like much of a friend by the way you talk about yours. Are you an Einstein? Do you think you have never talked about sh*t on a date that bored the guy you were with? If you truly care about her like you say, you would have mentioned her good qualities and your letter would have been concerned with helping her to bring them out. Good luck to her.

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