Ask Wendy

My Boyfriend Won’t Set Boundaries with a Female Friend – Help!

Friday, January 18, 2019
Hey Wendy,

I’ve been in a happy relationship for almost seven months now, and it’s pretty serious. We’re both in our late forties, have solid careers, and tidy endings to our first marriages. My guy has been divorced now for over ten years, and his ex-wife is lovely.

Here’s the problem: Several years ago, my boyfriend met a woman who turned into a friend who trains for Marathons with him. She’s about 10 years older than he is, says she’s in love with him, and has been the #1 reason for every breakup he’s had since she’s known him. He says they’re platonic, and he’s told her that nothing would ever happen between them because he’s not attracted to her.

She acts like a jealous girlfriend (calling over and over until he picks up, berating him, etc.) and he lets her do it. He’ll say, “I better pick up or she’ll just keep calling.” He doesn’t have any boundaries with her. He’ll even talk to her at really inappropriate times (like when we’re being intimate).

A marathon is coming up and they’re in training now. It’s been awkward since they are used to sharing a hotel room. He asked me if I was okay with it, and I’m not. He told her, “I can’t share a hotel room with you because Sarah has an issue with it.” He’s willing to put in boundaries when I’m to blame. And he said he would break off the friendship with her if I need him to, but I don’t want to be the cause of a friendship ending, but I don’t like what’s happening either. Help!

Sarah D., San Jose, California

Hey Sarah,

I take issue with this woman being the reason every one of your guy’s previous relationships ended. It’s not her who’s the problem—it’s your guy.

Let me help you out here. Instead of responding to you, I’m going to talk to your guy for a second. Please print this column out and hand it over to him. Okay? (more…)

I found my boyfriend’s sex tape

Friday, January 11, 2019
Hey Wendy,

I was scrolling through my boyfriend’s Mac and I found a large video file in his Photos. I opened it and saw that it was a sex tape starring him and his ex. I didn’t watch all of it, but I saw enough to freak me out.

I asked a friend for advice and she said I should confront him about it. I did, and I tried to be calm about it at first. He was shocked. He said he didn’t know it was there, and forgot it even existed. He deleted it immediately.

Should I be angry? It’s not like he is cheating on me. And he has every right to keep photos and videos of his past relationships. But I feel betrayed. He was incredibly apologetic about it, but deep down, it still doesn’t satisfy me. I’m not sure what I need, but I’m just really angry. And it makes me even angrier to know that my feelings are probably unjustified.

Terry R. - San Jose, California

Hey Terry,

Youfeel betrayed? Let me see if I got this right…

You broke his trust and violated his privacy by snooping through his computer. You found a sexy video—something he had every right to both make and have and that you had no business seeing—watched it, and somehow now you feel betrayed and he’s the one in trouble.


Just like you feared, your anger and frustration over this are unjustified. (more…)

How Do I Deal with My New Boyfriend’s Children?

Friday, December 21, 2018
Hey Wendy,

I have been in an amazing, satisfying relationship for the last 2 months with a widower. The connection is incredible, high level of maturity, strong, honest communication about needs, deal-breakers and sexual desire and negotiating deals. We are both over impressing each other, pleasing each other and more onto being ourselves and showing up as we are. Huge credit to your online courses in allowing me to be in such a blissful partnership.

We haven’t made our relationship known to anyone yet due to his situation. His wife was killed almost a year ago and his children are still grieving. He told me about this at the start.

He wants to introduce me to his family and friends; and we talked about waiting for the right moment. My question for you is how do I deal with his children once he breaks the news? His daughter (30) is married, and his son (27) is engaged. Any wise tips/ thoughts as I don't think this is going to be easy on them.

We are both very happy together and I want to be able to support him when the time comes. Thank you for all your guidance.

CM from Dubai

Hey CM,

Congratulations on finding a good match for you and creating a happy relationship! I’m grateful my courses helped.

I understand and appreciate your natural desire to step in and help with this huge adjustment for his family. I’d want to do the exact same thing. Here’s the rub, though—you can’t. (more…)

How Do I Handle Holiday Drama with My Husband & Family

Friday, December 14, 2018
Hey Wendy,

My husband and my father don’t get along, and after their last argument at Thanksgiving, my husband doesn’t want to go back to my family’s house for Christmas. How do I handle this?

Cherry T. Des Moines, IA

Hey Cherry,

You have a ton of options here. Want to know what is not in my plans-for-a-happy-holidays list of options for you? Suck it up and show up. And this is unfortunately exactly what many of us do all over the world this time of year.

“Suck it up” is terrible advice. (more…)

What’s the Story About Chemistry, Again?

Friday, December 7, 2018
Hey Wendy,

After reading your book, I've been inspired to 'up' my dating game. I've been going on dates with a lot of guys (go me!) and have felt all kinds of feelings for the various men I've dated: from repulsion to strong chemistry, to nothing. I understand that chemistry can be dangerous and lead you up the garden path (since you are blinded by those hormones going crazy) but you at least know there is an underlying attraction of some kind there. I wouldn't bother exploring something where I felt repulsed by a guy so that one is easy—no second date for him. What I'm worried about is whether I'm writing off all these guys in the middle (the middle being the guys I date that I don't really feel anything for: you know, we have a nice enough night but that's it).

I dated one of these guys recently. When I met him in real life, I didn't feel remotely physically attracted to him, however, I also wasn't repulsed by him. He was a lovely guy and I felt we shared the same values (I guess you could say he was in my 'tribe') so I wanted to explore things with him a little bit. But by the time it got to the third date and I felt myself hastily saying goodbye at the end of the date so that he wouldn't launch in for a kiss, I figured that wasn't a good sign and ended it afterward. They say that attraction can grow but is the dates enough to see whether that changes, or am I writing someone off too quickly?

I'm not expecting that the guy be exceptionally handsome, but I want to feel some level of physical attraction right from the beginning. Am I asking too much? I've been on a lot of dates and I'm starting to feel a bit deflated that I'll never meet someone that I'm physically attracted to that also ticks the other important boxes for me.

I would really love to know your thoughts on when to give a guy another date. I know you say listen to your gut, but unless there are some really big red flags, my gut is usually pretty quiet in the very early stages...I need some Wendy guidance! I would also really love to know how you felt about Dave, your #121 first date, on the first few dates.

Thank you,

Annie D., Australia

Hey Annie,

Thank you for reading my book! As you know, I hate rules, but in this case, I’ll make an exception. I recommend you give a guy at least three dates to see if he has that slim chance of growing on you. But this doesn’t apply to every guy who says, “Let’s do this again.” This offering is only for the ones you really like and deeply respect—as in the ones you wish you were attracted to. I mean you gotta really, really, really like him. (more…)

Why Can’t I Get Past Date #1?

Friday, November 23, 2018
Hey Wendy,

I’m now 72 years old but people think I’m 60. I’m young at heart, and I exercise regularly. I have quite a few men contacting me, but I don’t seem to get past the first date. We have lively, fun conversations, and sometimes we’re even together for three hours. What’s my problem?

Louise C. – Saratoga, California

Hey Louise,

I wish I could be there with you to see what’s going on and give you the why!  Why, why, why aren’t you making it past the first date? Since you can’t put me in your pocket and take me with you, I’ll start by asking you three questions: (more…)

How Do I Know if We’re Compatible?

Friday, November 16, 2018
Hey Wendy,

I’ve recently started dating a guy and he seems great. However, he seems to be a big drinker. I love a glass of wine and socializing but I’m not a massive drinker—and I also like to watch my weight.

We’ve been on eating and drinking dates so far, though I did arrange one game of putt-putt.

His life seems to revolve around going to the pub. I’m worried he’ll just want to go out drinking with me all the time, which I’m not keen on. Does this mean we’re not compatible? Maybe it’s what many single guys do?

Katy T – London, England

Hey Katy,

I’m happy you’re seeing someone you like, that’s fantastic! Now it’s time for you to add in the next element to your dating process. Most of us think of dating as fun adventures going out on dates; that is a huge part of dating, but we shouldn’t’ skip the important step of actually exploring compatibility while having these adventures. Compatibility goes far beyond things like he’s cute, fun, and good in bed (although those things are not to be dismissed). Will your day-to-day lives and everything they contain mix, or will they separate like oil and vinegar?


How Do I Meet Mr. Right as a Single Mom?

Hey Wendy,

How does one deal with being a single mom and dating/looking for your soulmate? I ask because I am a single mom and my most recent ex wanted me to put him before my kids. It was a very toxic relationship since the start and lasted 4 on/off years! He was an insecure, anxious, needy, controlling, macho man. Any insight is greatly appreciated.

Nohemi B – Sacramento, CA


Hey Nohemi,

In answering your question, I’m going to take a moment and ask everyone to get on board with me here—men, women, and gender-nonconforming alike, listen up. I have a very important public service announcement for you. Ready? (more…)

Dating While Rich & Successful: A Steve Jobs or A Stedman?

Hey Wendy,

I’m a doctor who owns her own practice. I also own twelve houses. I’m financially very successful. I’m fortunate with a net worth over ten million dollars. Is it realistic to ask for someone with equal net worth or education?

Rita L., Los Angeles, California


Hi Rita,

Congratulations on using your talents and education to make a successful life for yourself. Big kudos! I’m guessing you’ve already learned that success and status bring with them some unexpected complications. There’s that niggling question:

“Will they love me for who I am, or do they just want my _____?” You can fill in the blank with money, lifestyle, or access to opportunities—sometimes all three.

This shit is real. You can’t get around it, and it’s why you (and others with wealth and/or status) naturally want to partner with those in similar situations.


Why Are Online Daters Not Efforting?

Today we’ll hear from Kristen & Annie

Hey Wendy,

I’ve noticed an increase in men whom I’ve connected with online/dating app who completely drop off when I suggest we go from texting to a phone call, often with the intention to see about meeting up for the first time in person. I’m an introvert, and not a huge fan of chatting on the phone, but it seems like a very reasonable way to get to know someone before setting up a date. Part of me thinks well, if they can’t participate in one phone call then just move on; however, since this is happening often, it’s making me pause and question my strategy. Where are the men who have the basic social skills to go from online to in person with one phone call in between? I mean WTF?!

Kristen in Davis, CA


Hey Wendy,

In Australia, Tinder is by far the best platform to meet men. and aren’t popular here. Most men have a fairly short bio (if at all), and due to the nature of the app, once you get a match, messages are generally sent as short texts rather than wordy emails. I find myself chatting to a lot of men (most of whom initiate the conversation with me) that just do not seem to know how to ask questions! In my messages, I will reveal a little something about myself and then ask a question to keep the conversation going. I try to keep the chat fun and interesting.

I’m getting frustrated and I presume that this is a representation of his real-life character. I mean, if he simply replies with a statement and no question in each message, it seems like he’s either very self-focused or clueless about how to talk to people, right?! After speaking to quite a few single women, this question-less conversation thing seems to be a relatively common problem. A different, but equally frustrating subset of men are the ones who use generic emails for everyone and don’t pull out anything personal. Am I being too judgy?

Annie, Melbourne, Australia.

Hey Kristen and Annie!

Thank you for giving voice to an issue that so many women around the world experience. Yeah, dating is frustrating—I hear you! There are a ton of guys who have zero game; daters who are clueless about how to succeed by paying just the slightest bit of attention to what makes up basic conversation; there are people who have no intention of ever meeting you face to face and are just reaching out because they’re lonely; and then there are the bots (i.e. not even real humans!) writing you text messages using basic emails and scripts that pull keywords—sorry about that.

And yet, dating sites/apps are still your best source for gaining access to real, live, amazing people you do want to date and who you don’t have access to in your everyday world.


Why Am I Getting Ghosted After Sex?

Hey Wendy,

I am so glad to hear you say that there is no rule to whether you have sex or not on a first date. I have not gone that far on a first date yet but I tend to do other sexual things. I do let them lead and it is always a mutual decision. Afterward, the switch goes off in them and I get ghosted. I don’t know where the disconnect happens. I’m afraid I come on too strong because I ask where they think this might go and I am afraid that freaks them out. What are your suggestions to not get ghosted on the first date after they seem completely into you?

Nichoal E – Chicago, IL


Hey Nichoal,

I know a woman who, on her first date with a guy, had sex with him in a moving vehicle that neither one of them were driving. Those two crazy kids have been happily married for the past 20+ years, and they’re one of my favorite couples. I’ve talked to people who had sex on the first date with their future spouse in a bathroom bar, in a sex dungeon, and in a strip club (she was at a bachelorette party—she took him home and gave him a private lap dance for free). Now, I’m not saying that these are fool-proof, awesome strategies to adopt or the path to finding lasting, happy love. What I am saying is it happens.


If My Date Has Anxiety, Is That a Red Flag?

Hey Wendy,

I’ve just discovered your book and can’t wait to read it!

I am confused and hurt by a recent breakup and wanted to get your opinion on what happened. I dated a guy for about a month. In the month we got to know each other, he seemed like everything I could want in a guy. He was kind, easy to talk to, a gentleman, offered to pay on every date (I swooped the check sometimes though), and I felt like our connection was growing stronger with each date.

Because he’d done so much for me, I bought us tickets to see his favorite musician who he’s never seen live before. I was so excited to do this for him and knew we would have a blast. When I got to his house to pick him up for the date he told me he couldn’t go to the concert and he couldn’t date me anymore. He said he was going through personal stuff and his anxiety was getting to him. He missed where he used to live (he moved from North Carolina to the California Bay Area) and only had $2 in his bank account.


What Should We Be Willing to Change for Love?

Hey Wendy,

I went on a first date recently. Within the first 20 minutes of conversation, as we were both talking about where we live, my date mentioned that he could never live anywhere other than a big city.

Now, he was aware that I live in a regional town, one hour from the city. His comment really got me off on the wrong foot and I must say it bothered me for the rest of the date. I felt as though he was basically saying “I’m not prepared to move anywhere, so you would have to be the one to move”. Now living in the city and away from my family and friends is not what I really want, but it’s not a deal breaker and I would definitely do it for love. I guess what bothered me is that it felt like he didn’t have the same attitude and I wondered whether maybe he’s stubborn and uncompromising.

Or maybe it’s a deal breaker for him and he just wanted to get it out there. Or alternatively, it was an off the cuff comment that maybe could change down the track if he fell in love. Regardless, this comment so early on in our first date has stuck with me.

I’m not even sure yet how I feel about this guy, but I’m interested to hear your thoughts on his comment.

Annie D – Petaluma, California


Hey Annie,

Thank you so much for your question. Yours has to do with geography, but women everywhere find themselves asking some version of this question because we’re trained to think, “when he loves me, he’ll change.” (more…)

How Do I Stop Being Clingy & Too Needy?

Hey Wendy,

I think I’m ruining things in a perfectly good relationship due to my insecurities. I ask too much of my partner; mostly I ask for too much of his time, and I need a lot of reassurances that he loves me.

For his time, I try to keep busy when I’m not with him, and for assurances, I try to keep things to myself, but I rarely succeed. I have extreme abandonment issues and I’m vulnerable to codependency. Am I just fucked because of this? Is this a matter of finding some willpower? Do you have any practical strategies I can use?

Holly O – Savannah, GA


Hey Holly,

For extreme abandonment issues and codependency, I recommend you see a good therapist. If you can’t afford one, search the Google and find an online program or a book written by an expert (the ones with letters after their names) who can walk you through the process of healing and provide a practical process for doing so. In other words, if you can’t afford therapy, DIY it. If you’re shrewd in your selection and dedicated in your pursuit of change, it’ll work just as well. No one deserves to have their issues follow them throughout their lives, wrecking perfectly good relationships as they go—and as I think you know, they won’t go away on their own.


How Can I Tell When I’m Ready to Date Again?

Friday, September 14, 2018
Hey Wendy,

At 54, I’m in a financial pickle after a failed business endeavor. I own a house but have no savings and owe $15,000 in back taxes.

I’m bummed about my last failed relationships, am in therapy, but at least the breakup pain is no longer exquisite. Just low-grade sadness or bleakness. Relationships have always been my primary source of joy.

My house needs some decluttering and I’m in mid-repainting. I need to sell some items or give them away.

Then there’s the middle-age pudge that is too much to feel super sexy.

So, when do I start dating again and when do I know I’m ready? Should I spend another 6 months plodding along losing more weight, upping the income, improving the home feng shui? At 54, is there really hope for love again?

Stefani – Temecula, CA

Hey Stefani,

Great question!  Determining when you’re ready to date can be tricky. You’ve got to discern if you’re in good enough working order to be out there before you date. The good news is it doesn’t have to take you six months—in fact, it doesn’t have to take you six days if you’re motivated.

You, your living conditions, and your financial life do not need to be perfect, so let’s look at “good enough” one piece at a time. Ready? (more…)