Ask Wendy

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 can 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?

Finances: No savings and some debt? Okay. Sounds like many people. Not ideal, but not abnormal. I hear you that your inner critic has plenty to say about where you should be financially at 54 (mine is talking my ear off about it, too), but you are where you are. So, your responsibility as a single person who dates is twofold:

  • Be able to pay for yourself on a date when you go out. It’s okay if your date treats you, but don’t rely on it.
  • Be transparent about your financial situation with anyone you’re dating seriously. This is not a first date conversation; this comes later (much later). And it’s perfectly acceptable to go out for coffee, or a drink, or a walk in a (well-lit, high-foot-traffic…what, I’m a city girl) park, or to do other free activities.

Your home: You are ready to date when you are ready to bring someone back to your home and be okay with what they find there. If your house is lived-in and slightly worn, that’s different than hoarder-level stacks of stuff. If you’re approaching the latter, however (and I say this with love), sort your shit out. Get a girlfriend to come over and help you over a weekend or two, because some of those things you think you need to sell might need to be given away or discarded, and thinking you will sell them will only keep them around longer and prevent you from moving on in your life. Is that a price you’re willing to pay? Our cell phones make it super easy to throw things up on EBay or Craigslist now, so make it happen!

Your body: This is the easy one. If you want to lose weight, cool. You can do that. But it’s not a necessary prerequisite for dating. Did you know there are guys who like women at your size? It’s true! There are men who love your body just as it is. And there are men who will love your face, and the body aspect is inconsequential. There are also men who will love your energy. There are men who don’t care about the actual shape of your body but how you move in it. See? No need to wait to date—you are datable and sexy at your size. “Fake it till you make it” is your best friend here. Work on exuding confidence in yourself, even if you don’t feel it yet. And once he’s looking at you like you’re the tastiest snack in the room, you just might believe what you see.

Your mental health: This is the toughest one, and I’m going to defer to your therapist on this one. Check with them and see if they think you’re in “good enough working order” to date. Then after they give you their opinion, check with your gut to see if that feels right to you, and make up your own mind from there.

I will say that most of us look for stability and joy in another person, and girlfriend to girlfriend, I think that this is a bit of a mistake. You might want to use some of this single time to learn to enjoy being a single person, as fleeting as this time may be, because do you know who makes the happiest partners? Happy people.

Is there still hope for love and relationships at 54? Absolutely! But only if you say so. Have you ever noticed that we humans are always telling ourselves stories, and then we buy into the narratives we spin regardless of whether they’re actually true? I know a lot of folks who say, “It’s too late for me.” Okay. If you say so. Or, “No one will want to date me at this size.” If you say so. Or, “that person could never love me, they’re too hot/successful/smart/funny/unobtainable.”

Mmmm. If you say so.

There is not one thing wrong with being single, but if love and partnership are what you’re after, it’s available at 54, 64, 74, 84, 94 or 104. We’re the ones who put the brakes on what’s possible. Choose your story wisely.

Happy dating!

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.


Why Am I Attracted to Married Men?

Friday, July 20, 2018
Hey Wendy,

Why am I attracted to married men? I don't mean to be. And we don't really start anything beyond communicating as friends, but there is still that crush or attraction that I have to get over, or else I wait for it to disappear over time.

It's that excitement when you get a message, it's that general good feeling of being around them (and they're not always even my physical type).

I feel some guilt even when I tell myself it's admiration and it will eventually not cause the same excitement in time.

I don't like beating myself up over liking a married person for being a beautiful human being. But there is that attraction and fascination and I don't know what I should do with it.

Thanks in advance for your insights on this.

Dianne T. ~ San Jose, California

Hey Dianne,

If you absolutely know without a shadow of a doubt that you will never ever act on any of these feelings in any way, including flirting, then crush away. You have my blessing. Feel all the feelings guilt-free. That particularly sharp-edged zing we vibe on from the unobtainable can be delicious. And there is no shame in thinking thoughts.

Now, if you’re compelled to move beyond just a feeling that you keep to yourself, here’s why:


Should I Try to Reconcile with My Ex-Boyfriend?

Friday, July 6, 2018
Hey Wendy,

Should I reach back out to my ex-boyfriend to see if he's open to trying again?

My relationship ended last month, with a man whom I thought was "the one". I wasn't expecting the breakup, and needless to say, was heartbroken.

I mailed him a closure letter, and he actually mailed me one back. It was a very kind note, explaining that his breakup with me was not logical. He didn't feel like we connected in the way he hoped for, so had to listen to his heart.

Of course, I can't speak for him, but from my perspective, relationships aren't black/white, and we had chemistry. We "checked off" each other's boxes. He is highly sensitive, and more emotional than I am, but it didn't necessarily bother me. Except he could be high-maintenance at times. But I was willing to accept him because I loved him.

Anyway, he said to me a few times that he just wanted to be happy with me all the time. Which isn't really realistic, and I told him so.

Looking back at our relationship, there were a few moments where things didn't go perfectly, and we had miscommunications. I think it was those moments that led him to think things weren't going well. As well as the fact that I don't necessarily love everything that he loves, in terms of comedies, TV shows, etc., and he's told me he wished I did, so he can share some of his joys with me.

I think he wants a fairytale, hobbyist-type relationship, and it's not realistic, imo. Hobbies change, and there's no relationship that's always happy.

Is it a good idea for me to reach out to him, and see if he's open to seeing things from a different perspective and trying again? Or should I just let this one go?

Sabrina L – Dallas, TX

Hey Sabrina,

No! No, no, no, no, no, please, no.

There, now that we’ve got that initial primal scream of hell-to-the-no out of the way, I want to say thank you for asking my opinion. Circling back to see if you can go another round with this one is a bad idea—let this shishy go.


How Do I Stop My Husband From Interrupting?

Friday, June 29, 2018
Hey Wendy,

I’ve been married for a long time, and I’m struggling with a problem and would like your advice on how to talk to my husband about it.

There are times in my day when I’m focused on doing something like looking at my online calendar and preparing for the day; or getting ready to go out by doing my hair; or when I have my head deep in a project. What happens is my husband pops in and asks me important questions that would need my consideration, focus, dialogue, and decisions. He does this at times when I can't hear him or remember what he said. It’s distracting, but I don’t want to hurt his feelings or cause him to feel like I’m putting him off or making him wrong. What should I do?

Heather F. – Reno, NV

Hey Heather,

It’s maddening, right? When a partner breaks our focus or blocks the flow of our transition between tasks it’s like getting pulled into another world – their world. They don’t mean to do it on purpose; they just don’t notice they’re doing it. You sound like a nice person who picked a good person who means well, so I appreciate your sensitivity around this subject.


How do I Learn to Hold My Boyfriend to a Realistic Standard?

Friday, June 22, 2018
Hey Wendy,

When I first got into my relationship, I was happy. I didn’t make a fuss about too much. He was late all the time and I dealt with it. There were other things that I put up with but as time went on I noticed I couldn’t keep ignoring the things that bothered me.

Eventually, those things made me angry. If he was late, I “nagged” as he called it. I don’t like being a nag but at the same time, I dislike when people don’t respect my time. I notice that when my friends are late it does bother me, but I won’t argue with them for it either. I’m not sure if his lateness is what really bothers me or his ability to act like it wasn’t a big deal that he’s late. I’m angry nearly all the time in this relationship, not just because of the late thing but because he downplays every situation and it feels like my feelings are invalidated. I don’t want to be angry. We’re two years in and I don’t know what to do.

Linda ~ Santa Rosa, California

Hey Linda,

There’s an old Pagan custom called handfasting. Like an engagement period, two people would declare a binding union between themselves for a year and a day. It’s like a trial marriage. It gives the couple the chance to see if they could actually survive marriage. After a year, the couple could either split as if they had never been married, or decide to stick together for the long term.

I think this is genius because a new love’s charm often has us running straight at our target with our eyes wide shut. Then when the newness wears off: damn it! Turns out there are things that just aren’t tolerable about the person you were so sure was the right one.


Why Do Guys Pull Away or Say, “I Don’t Want to Hurt You”?

Friday, June 15, 2018
Hey Wendy,

What do men mean when they say they don't want to hurt you? It seems to happen after they've pursued you pretty hot and heavy, and now you've agreed to get more intimate with them. All of a sudden, they seem to put on the brakes and waffle about moving forward. They say something like, "Hey, I don't want you to get hurt," or "I don't want to hurt you." What the what??

Are they wanting to see if you're a grown ass woman who can take care of herself and her feelings once sex is on the table? Are they providing a disclaimer that they're going to be a dick in the future and they're covering their ass, having warned you from the very beginning? What should we know about this?


Hey Chloë,

When I was writing my book, 121 First Dates, I read a lot of other dating books to see how mine would stack up against the competition. There were raunchy ones and spiritual ones, funny ones and serious ones, and on and on. But the one thing they all had in common was employing strategy!

The spiritual one encouraged women to set a date, then break it last-minute—the “give, withdraw, repeat” technique. Wait, what?! Another gave a cockamamy analogy of asking your potential prince to dive under a moving bus to fetch a prize you tossed under it, and if he emerged with it for you, he’d be a keeper. Huh?!


My Boyfriend Makes Me Feel Bad When He Looks at Women & Porn

Friday, June 8, 2018
Hey Wendy,

I’ve had numerous issues with boyfriends in the past that my current boyfriend knows about. I shared these things and he seems to be using them against me.

For example, he will make me feel bad when I confront him about constantly looking at other women. He will make me feel bad when I confront him about watching porn whilst I’m gone for a couple of hours. He will make me feel bad when I tell him how bad he is making me feel. Can you help?


Hey Ellie,

I’m sorry your boyfriend is triggering hurt feelings in you; the situation sounds combative and painful, and I’m truly sorry about that.

If looking at other women and porn are deal-breakers for you, you could definitely find a new boyfriend who doesn’t do either of those things. But you are not going to change your guy. Not with niceness, not with directness, not with a new shade of lipstick. (more…)

I Like a Slut and I Don’t Know What to Do

Friday, June 1, 2018
Hey Wendy,

So, basically, I’ve been getting with this fit girl, she’s so out of my league and seems to want to progress things on. One problem is that she is known as a slag. She was with one of my friends on the same night as we got together. My head says bin her off but my heart says forget it and go for it. It’s tough to bin her off because despite the ‘slaggyness’ I really like her and don’t think I’ll get any better. Should I bin her off or forgive her and pursue it?

Jerry – Leeds, UK

Hey Jerry,

You say, “My head says bin her off but my heart says forget it and go for it.” Jerry, that’s not your heart, that’s your dick.


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