How Can You Tell If Your Boyfriend Really Loves You?


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I am 25 years old and I’ve been dating my boyfriend for 3 years. I’ve had a couple of relationships before him, one was serious.   He’s had several relationships before me but he told me he’s never been in love.  

We have a good relationship, we do lots of things together, have the same friends, we like watching sports together, we have a really good friendship. We do have some pretty bad fights, some important and some ridiculous, but we usually bounce back pretty fast. I really love him.

Up until a few nights ago, he never told me he loved me. I’ve been going through a rough transitional period and feeling very insecure.   He just started a new job as a teacher and his life seems pretty set.  

We’ve had conversations in the past about marriage and he would always say he wasn’t sure if he wanted to marry me, but he knew he wanted to be with me. I never put any pressure on him to tell me he loved me or marriage or anything else.  

I’ve been really depressed about my life lately and the other night we had a fight and after we were talking things through. He went to bed but then called me over to lie down next to him. He said: “I’ve been doing a lot of thinking about you and our relationship, and I want you to know that you really mean a lot to me. I’ve never felt this way about anyone before and I want you to know that I do love you. You deserve to be loved.” I started to cry a little, hugged him and told him how much that meant to me. He said he doesn’t want to say it all the time, only when he feels it and that he never wanted to say it unless he was sure he wanted to marry that person. I’m positive that he still doesn’t know if he wants to marry me.  

My question is:    

Does it sound like he told me that to try and make me feel better, because he felt bad for me? I want so badly to believe he really loves me but I’m starting to think he said it because he felt he had to and thought it would make me feel better. I have a tendency to over analyze things and I don’t want to ask him a million questions and make him regret telling me that. How can you tell if your boyfriend really loves you? I know I must sound crazy. I’ve been going through a rough time and I’ve been having trouble processing thoughts and emotions. I would appreciate any thought or advice you might have to offer.

Thank you,


William Goldman said this about Hollywood, but I’d say that it’s more apropos in describing matters of the heart:

“Nobody knows anything.”

That’s right. I may be a dating coach, but I’m not omniscient. I certainly know less about your life and your boyfriend than you do. So whatever I’m doing here is just making an educated guess.

I’ll admit, I was a little choked up when you got to the part where he told you that he loved you. It’s really hard for some guys to say those words, and that’s not just an excuse for my gender. Since women place such great meaning on “I love you”, men have learned to adapt in one of two, super-logical ways:

Saying they love you without really meaning it.

Not saying they love you until they’re really, really sure.

Sounds like your boyfriend is in the second category. And yet, you’re not sure if you even believe him. Well, what could he tell you that would make you believe him? “I love you-will you marry me-here’s a ring-do you believe me now?”

You’re really asking two different questions here, Lisa.

You want to know if he means that he loves you.

You also want to know if this means he wants to marry you….

I would say that, from what you wrote above, I do believe he loves you and that he doesn’t know if he wants to marry you. Understand that this is not a contradiction. Love happens before marriage. That doesn’t mean that marriage results every time two people are in love. If it did, most of us would be married a good three times before we’re 35.

The reason I believe that your boyfriend loves you is because he did make a big deal about not saying it unless he meant it. And if it took a moment when you were feeling sad and vulnerable to allow him to express his feelings, so be it. Men want to make you feel good. They want to be your heroes. Trust in that.

The problem is that you’re looking for clarity. You’re looking for definites. But there’s no value in asking a question to which you can never actually know the answer. It’s a ticket to paralysis.

Think of it like religion. You can either 1) take a leap of faith, 2) agonize over not knowing, or 3) accept the fact that you’ll never know. I choose the latter. After all, nobody knows anything. We’re all just guessing.

I get why you want to know if he’s in love, but the truth is that he probably doesn’t even know. He said it once and I believe he meant it.

But just because he loves you now doesn’t mean he’ll love you forever, and just because you love him now doesn’t mean you’ll love him forever.

There are too many variables, too many unknowns.

So don’t spend your time questioning him. You’ll just drive yourself (and him) nuts. Continue to love him, continue to let him invest in you and open up to you, and if you’re not getting the consistent feedback you need to feel secure, you know what you need to do.

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


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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.

What Do You Do When a Guy Talks About Himself All The Time?


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Had a date that I met on-line a few weeks ago. Just went for coffee and a muffin (first date). However, I have run into this situation many times and do not know how to handle it. The date (male) spent the whole time talking about himself. Asked nothing about my life. Had two conversations with him on the phone prior to our meeting, and all he did was talk about himself. (There was “the writing on the wall.”) He was attractive and polite and seemed decent but there was this issue.   I was not his type anyway, so he is out of the picture. However, this problem still needs to be addressed. I also dated someone for a few months and he, also, talked about himself only. Was thinking of seeking professional help with this one since it is common. Thought of saying, if it comes up again, “How about we spend the time we have dividing the conversation between half of the time about you and half about me?” Is this a realistic tactic or should I just write the person off?  

Please advise.


Dear Jackie,

Did I ever tell you about the time that I was out with this woman from JDate?

We had talked on the phone for a little bit before meeting, did a bunch of IMing, but when we went for drinks, she must have had a three hour monologue prepared. I couldn’t get in a word edgewise. The fact that I ended up making out with her that night couldn’t disguise my utter contempt for her disinterest in me. Her four minute long voice mail when I never called again was an instant classic.

And then there was the time that I met a JDate girl on the phone who had recently broken up with her boyfriend of six years. And when I asked her if she was really ready to date, she gave me a very detailed explanation. It was more of a dissection, really, of everything that went wrong between the two of them. Finally, when I sensed that my “uh-huhs” and “yeahs” didn’t seem to matter much, I put down the phone and went into the bathroom. From there, I proceeded to take off my clothes, brush my teeth, wash my face, take out my contacts and return to the phone, where this poor woman was STILL talking about the demise of her relationship. I never ended up making out with her, since I told her that I put down the phone on her. True story.

Oh, I’m sorry. Did you ask a question? That was so rude of me.

So enough about me. What do YOU think about me?

My apologies for all the jokes, Jackie. But what else can you do but laugh when your dates go horribly awry?

Thankfully, you’ve already taken responsibility for your minor part in the bad date; namely, that you shouldn’t even have gone out with the narcissist after your one-sided phone conversations.

But I do think you’re sort of missing it if you’re going to try that clunky line about dividing half of the conversation. Honestly, you’re not splitting a cake here; you’re supposed to be getting to know each other.

Conversation is like a tennis match — it’s back and forth and it takes two people to take a game to the next level. If you’re hitting volleys and he’s hitting the ball to himself, well, it’s no surprise that your matches haven’t been particularly memorable.

But you already know this. What you may not have considered is that good conversationalists aren’t necessarily the best talkers. They’re the best listeners. And sometimes, by being a good listener, and asking the right questions, you can create an opening for your date to be a better listener as well….

Believe me, it’s not a perfect science. You may ask a question that unintentionally leads to a twenty-minute diatribe about his office politics. By the same token, you may subtly steer the talk down a different road, one that applies to you. That’s when you need to jump in and share YOUR stories. Don’t wait for an invitation from him. Just listen to him tell you about his timeshare in Puerto Rico, and then bring up your tales from Costa Rica. If you’re a good storyteller, he may even want to ask a question about it. (Or, more likely, start telling you about his upcoming trip to the Bahamas).

Frankly, I think most folks are good people but very bad daters. They see the date as one of two things. First, they see it as an audition, a chance to impress their date with all of their credentials and A-List stories. Then there are those who see a date as an interview, where they’re the boss, trying to suss out the serious candidates. Those are the kind people who ask you if you’re serious about getting married before they even find out where you grew up. The problem is that both people — the show-off and the boss – have an agenda — either to impress, or to not waste their time.

Both agendas are unattractive.

The one thing I would implore you to do differently is to forgive these yappers for their clueless sins. They might as well be third grade boys who are pulling your hair for attention. I’m not saying you have to like them, or that you have to go out with them again. All I’m saying is that these guys are trying to share a piece of themselves and are hoping that you’ll eagerly receive it.

What they haven’t yet realized is that the way to your heart is to LISTEN to you.

But that’s another column for another day…

How to Start a Relationship When You’re Out of Town


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I have a client who is dating online. He’s gone from nothing to raining women in a few months. Except most of the women with whom he’s corresponding are out of town.

So while he’s visiting one right now, he hasn’t yet booked a flight for the one he’s really excited about.

If he sounds a bit shady, he’s not. He’s just overwhelmed by the choices he’s created for himself – to the point that he’s not actually thinking straight.

He asked me how he should play it, given his level of interest in the second out of town woman.

Him: Is it all right to let her know that I’m going to be out of town for awhile?

Me: Sure.

Him: Is it all right to send her an email while I’m gone?

Me: Sure.

Him: Do I have to call her if I’m away? Or can I just wait until I get back?

Me: You’re going away on business for two weeks, with a little bit of pleasure. How do you think she’ll feel if you don’t speak to her for two weeks?

Him: Yeah, I guess.

Me: This is the one you really like, right? The one who you talk to until midnight?The one who flirts with you and teases you? The one you really wanna meet? So let’s pretend you weren’t going to play any games or strike any postures to achieve a certain result. How would you act toward a girl who was really into you? How would you act if she was your girlfriend?

Him: I’d call her. I’d probably call her all the time.

Me: Because she’s your girlfriend.

Him: Yeah. That’s what you’re supposed to do.

Me: That’s what you want to do. Do you want her to be your girlfriend?

Him: Maybe. Sure.

Me: Then start treating her like one.

Him: Got it.

Not until then did it occur to me that in three of my most prominent adult relationships, the bonds were forged when we were in different cities. I’m not just talking about long-distance. I’m talking about meeting someone right before I had to go visit my family for a week. Each time, I followed through on the early promise of our email/phone conversations and allowed myself to drop my guard. Each time, I came back to a woman who became my girlfriend.

By making an effort while you’re out of town, you show in actions what no amount of words can say: that you’re serious, that you care, that you can’t wait to talk again, that you refuse to lose the tenuous connection that you’ve forged thus far.

Of course, it takes two to tango. If he emails every day and she doesn’t email back, there’s a major power imbalance. But if he makes an effort and she makes an effort, I can virtually promise that by the time those two get together, they’re going to be a virtual couple. No one can predict whether there’ll be chemistry, but we do know there’ll be trust. And trust, if you’ve ever dated online, is even harder to find than chemistry.

Let down your guard. Show you care. Make an effort.

You can’t lose by being real.


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