Ask Wendy

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…)

Is My Long-Distance Relationship in the Friend Zone?

Friday, September 7, 2018
Hey Wendy,

So, I met this guy during my travels. We were at a dinner with mutual friends.

We hit it off and started talking as friends through texting every day, sometimes until late at night. Once I returned to my country, the communication continued consistently for months, even until today.

Last May I decided to book a trip to see him to see how it would go. We ended up living under the same roof for a month. Things went well, we had a great time spending all that time together. It does feel friend-zone to me (no kissing or sex or anything). We just spent time getting to know each other.

A few days ago, I finally asked him how he feels about me, and he said he isn’t sure how he feels. He thought it wasn’t anything more than friends after the trip was over, however, we kept talking after the trip and now he’s not sure how he feels (again). He enjoys my company and he’s comfortable with our silence, which he rarely has. He said he’s scared to lose what we have, and that I mean a lot to him, he doesn’t want to hurt me. What do you think I should do? Thanks.

Tracy L. – London, England

Hey Tracy,

You are his friend, and that is all. You can continue to be his friend if you’d like to, but disavow any notion that you’re anything more to each other than pals. Do this is for you—not for him.

Here’s what I think you should do (and thank you for asking!): (more…)

Is My Boyfriend Bisexual and Cheating?

Friday, August 31, 2018
Hey Wendy,

A couple of months ago, I randomly looked through my boyfriend's phone and found hidden craigslist emails responding to personal ads. The emails revealed his phone number and our street address. We've lived together for over a year, and I'm a part-time mother his two girls. The people he’d been replying to were ads from old men looking for young guys, men, pregnant women, and just anybody and everybody. These emails went back before we were dating and have continued throughout our relationship.

I confronted him about it, respectfully at first but he tried to lie about it. Eventually, he got more truthful but wouldn’t give me real answers to my questions. I am unsure if he ever met up with these people, but when I asked why, he said, “It is like a game to me. I do it for the thrill.” I told him if it happened again I would leave. After that, I went through a range of emotions for about a week before I got over it.

Yesterday, I asked if I could use his phone to look up a frozen yogurt joint. I go into Google, and the last thing he looked up was “bi swinger life”. I shoved the phone in his hand and said I had to leave. We started yelling and he said, “We already had this conversation and I paid my dues! You can’t keep punishing me. I didn’t do anything I swear!”

I don’t know what to believe. I don't understand how a woman can date a bisexual man, how do they do it? It might have been different if he told me in advance, but I found it out the hard way. And I can't get over that he was talking to everyone, including old men.

We are in a long-term relationship and planning on kids and marriage and a house in 2 years. He is a sufferer of PTSD from Afghanistan. I know I am the only good thing in his life and the only person who cares. He knows that he needs me and that I am his last chance at a happy life. But how am I to get past this? He won’t talk to me about it. What if he cheats with another man? If he loves me and wants this marriage and life, then why isn’t my love enough to curve his curiosities and be satisfied with me?

Brittany W - San Diego, California

Hey Brittany,

Wow, there’s so much to unpack here. I’m sorry for the shock and the hurt this is bringing to your life. You have every right to be pissed that he’s been sneaking around and lying to you about who he is. I’m sorry you’ve been lied to.

Nearly every relationship expert on the planet would stop right there. He lied, you have a right to be pissed, and that’s the end of it. But I think there’s more to the story. Sixteen years of studying men and sex have taught me a few things, the first of which is that men will only tell you who they are, what they’re thinking, and what turns them on when three conditions are met: (more…)

I Don’t Understand How Sex & Dating Works

Friday, August 24, 2018
Hey Wendy,

I am new to dating, and in trying to figure out what I’m looking for. Not being able to enjoy experimenting and exploring sex and touch in a relationship is a deal breaker for me, and I would like to meet someone with a similar sexual appetite. And I’m also looking for a committed relationship.

The two biggest pieces of dating advice out there are to:

a) Not have sex and talk about sex too early
b) Don’t go for the guy you are strongly sexually attracted to

How do women dating today assess if a date is compatible sexually?

I appreciate your thoughts on this.

Shelley L ~ Albuquerque, NM

Hey Shelley,

Those two dating tips on heavy rotation are in place so you don’t lose your mind. When we entangle ourselves sexually with someone very quickly and it’s good? We do, in fact, lose our minds (temporarily, of course).


Why Am I Attracting Men Who Only Want Sex?

Friday, August 17, 2018
Hey Wendy,

I stepped out of my comfort zone and started online dating about a year ago. I've had no shortage of matches (it's the red hair) but all of my dates turn the conversation to sex at some point before we even meet. Sometimes it's in the first few text messages, "You're a BBW?" Or if it's a last-minute text asking, "Why don't we just skip drinks and meet at a hotel instead?"

Growing up as a curvy girl, I always felt self-conscious about my body. It took years to come out of my shell. Now that I'm in my late 30's, I've been embracing my curves and little by little I've been feeling beautiful and sexy again. I'm attracting a lot of 20-somethings, it’s helped me feel more confident.

But I want to know, why am I attracting men who only want sex and not attracting men who want to get to know ME? I'm exhausted from having the same conversations leading to the same disappointments. I'd love to date respectful, chivalrous, alpha men in my age range. How can I project in my online profile that I'm worth getting to know...that I'm not just online looking for a one-night stand?

Andrea I - Iowa City, IA

Hey Andrea,

Let me tell you something about men.  When it comes to dating, there are two kinds:

  • The kind that only want to have sex with you
  • The kind that want to have sex with you and get to know you.

This is a common misconception—thinking it’s either “sex” or “get to know me”—but it’s not or, it’s and.


How Can I Help My Unemployed Boyfriend?

Friday, August 10, 2018
Hey Wendy,

I've been dating a guy for 3 months. He recently lost his job and now he doesn't want to hang out. Every time we talk on the phone, he complains how horrible his life is. I of course want to be there for him. But he keeps pushing me away. I got a new job and he didn't even ask what it was. Do I leave him alone and let him call me? What does he want from me?

Emmarie D – Santa Monica, CA

Hi Emmarie,

I’m sorry that you’re going through this bumpy time in your new relationship. Honestly, I don’t know what he wants from you, so you’re going to have to ask him. And girl, this is not the time to be gentle or beat around the bush. Do it like a dude: Direct, to the point, no messing around. Try something like this:


Is he Into Me or Not?

Friday, August 3, 2018
Hey Wendy,

I'm dating (again) and here’s what’s happening over and over:

Scenario: We start writing online, I reply with a short but personalized note and ask an open-ended question to make it easy to keep the convo going. He replies with a short answer to my question but has no launching off point for continued conversation or any follow-up question(s) for me.

I reply with "Oh that's great" or "Sounds fun/delicious/entertaining/..." and leave it there and usually, he doesn't reply or does reply with a similarly non-stimulating short reply. My general approach has been, "He's not really that interested." And I let it go.

One of my (married) male friends gave me his opinion, which was “You should interpret any reply as interest, especially if he took the energy to answer your question."

Since then, I’ve tried keeping it going... but I've found when I take this approach I feel weighed down.

Any thoughts, reframes, or approaches that can keep it fun and have me not feeling like the steam engine generating the conversation?

Paisley- Lovington, VA

Hey Paisley,

Yeah, your married friend is wrong. Not his fault—he’s working with a skewed perspective because he has access to the attentions of his wife whenever he needs it.

For a single guy, even when uninterested, sometimes it’s worth taking a moment to fire back a quick answer to the cute girl who emailed you just to get another little taste of kindness, indulgence, or thoughtfulness. This, however, is not your job.


Why Don’t Men Approach Me?

Friday, July 27, 2018
Hey Wendy,

My friends ask if I get hit on a lot and I don’t. They are dumbfounded. They say, “I can’t believe men are not all over you because you’re strikingly beautiful.”

Men don’t approach me. Ever!

I know I must be sending out weird vibes. How can I overcome my awkward, scared nature when I am in the company of men?

Beverly W - Chicago, IL

Hey Beverly,

I could toss you a trite and simplistic tip like, “a stranger is a person just like you. They feel awkward and scared, too” but it won’t help guys approach you in public.

Never in all of history has it been tougher to meet people out in the world than it is now. The following might seem like a random tangent but bear with me.

The #metoo movement has caused a new awakening around consent, which is awesome! We needed it. Men are rising in the public eye in droves and they now understand that some of their actions toward us can feel threatening.