Ask Wendy

Dick Size Dilemma & Dating with Dollars

Friday, November 18, 2016

My husband has a huge penis and sex with him has always hurt. I haven’t said anything because I’m not sure there’s anything that can be done about it. Can you tell me if there’s a way sex can be better for me?

We women know the struggle is real, yet guys always make such a fuss about dick size. I wish everyone could get on the same page on this issue. Say it with me: It’s not the size that counts—it’s the fit. And an extra large peg trying to cram its way into a small hole sounds more like “ouch!” than “ahhh.”

This is a tricky one because all the good advice in the world won’t help if you two are too far apart in size. If this is the case, you’ll be limited to just a couple of options I’ve presented below, but hey, a couple’s better than none. Ready for my suggestions? Buckle up!

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Trumped & Tripping Through the Land of Polyamory

Friday, November 11, 2016

My partner is upset and somewhat inconsolable about the election. I’m worried. What can I do? We’ve been Trumped.

Dear Trumped,

I hear you, sister. Half (or more) of our nation is in mourning and worried sick right now. We all have work to do to bring peace, our values, and safety to those we love and those we care about. So let’s start at home.

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Sexy @ Every Size + Getting Him Off the Couch 101

Friday, November 4, 2016

I am not at my ideal weight. I don’t feel sexy, so I don’t date or pick up on cues from men. Any tips?

“Look, with my luck, I will starve myself, work out, reach my ideal weight, and then the next day get hit by a bus.” —Drew Barrymore

I’ve never met a woman who thought she’d reached her “perfect” weight and shape. Ever. The misstep here is avoiding engaging with guys because you believe your sexiness is tied to the number sewn into the back of your sweater.

We’ve had it pummeled into us that there’s only one kind of sexy: skinny, voluptuous breasts n’ booty, and feathery white wings shooting off your shoulder blades as you strut down the runway in slinky lingerie. Oh sure, we’re willing to make the occasional exception for, say, Christina Hendricks. Our society has lost its ability to distinguish reality from fantasy, and there’s very little room for anything other than that one unattainable-to-the-masses shape.

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I Ain’t Afraid of No Ghosts ~ Halloween Edition

Friday, October 28, 2016

Okay, I’m trying to get past a guy who “ghosts” me…again and again. How do you get past your past and really find Mr. Right?

It’s much quicker to move past (and away from) someone who’s behind you rather than right in front of you.

You aren’t stuck with that ghost, even if he’s intermittently haunting you. You move past your past by leaving it exactly where it is and skating two long strides forward. Pay attention to your present, and daydream about your future ~ without him in it.

It’s tempting to indulge in daydreams of the things that you like about him, those feelings of delight and desire that are both familiar and exciting. But when the sensations are an entangled mess of pleasure, pain, and deep-rooted twinges of abandonment and unworthiness, the sweetness turns bitter.

So don’t feed the ghost. Instead, try these two experiments:

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How to Say “Thank You, No Thank You” 101

Friday, October 21, 2016

Series conclusion: What causes a relationship to go into a downward spiral? #5. Not making each other top priority.

You couldn’t stand the thought of being apart from him when you crazy kids met. But after a year of living together, you’ve picked up another kickboxing class (or two), slid Wednesday girls’ night back into the calendar, and turned Saturday into work-from-home-in-your-sweatpants overtime day.

A year or two later, kids come along, and it turns out the little buggers are dependent on you for pretty much everything. Assigning them as your first priority is the responsible thing to do, right? You’ll still find time for your honey in there somewhere.

But where?

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“I Need More” & Criticizing the Crap Out of Everything!

Friday, October 14, 2016

Series continuation: What causes a relationship to go into a downward spiral? #4: Never let anything be good enough, and criticize the crap out of everything.

Most of us women hate criticism. We hate it. But we take it if it’s good advice. Do you know if a random street person off their meds told me I looked ugly in purple, I may never wear that color again? It’s true. Hopefully, unlike me, you consider the source before you change your habits (or your sweater), but you get the idea.

We make changes in our lives based on outside influences, pressures, and suggestions all the time.

Because we assume men are the same, we often use criticism as a way to get them to change, to do something we want them to do, to stop doing something we don’t, or to just get them off the goddamned couch and take out the trash already.

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Be Happy & Trust Men: Piece of Cake, Right?

Friday, October 7, 2016

Series continuation: What causes a relationship to go into a downward spiral? #3: Being Unhappy

I’ll be happy when…

  • I meet him
  • My finances aren’t so out of whack
  • My kids are happy
  • My health is better
  • He marries me
  • I finish (fill in the blank here)

This list? It’s a trap. And it’s not true. You’ll be happy for about five seconds until you see another thing that needs to be accomplished, then another and another, and soon you’ll be right back to feeling down on yourself.

Happiness is something that we all look for, hope for, or are envious of in others. A lucky few of us understand that happiness is a constant choice, not a circumstance or static state of being. Happiness is a place to come from within ourselves, and even knowing that, we sometimes fail at being happy.

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Stay New & What Happens When You Get Your Drink On

Friday, September 30, 2016

Series continuation: What causes a relationship to go into a downward spiral? #2: Letting Go of the New

When you met your beloved, he was cute, cute, cute! Part of what was alluring was the mystery. Hallelujah and amen for a sexy and exciting man. Was he the person you had been praying to every imaginable God to meet one day? Would he feel the same way about you? Could you exhale with this one? What makes him tick?

The magical combination of chemistry, newness and uncertainty trigger a whole lot of hot, Eros lust. The start of a relationship is where sexual tension, steaminess and adventure dwell. And as you got to know him, and as your lives moved from two single people to two peas in a pod, you took pleasure in the discovery of this new person, right down to finishing his sentences. Knowing him afforded you confidence: You could bet that your chicken casserole would become his favorite dish, you could successfully purchase the socks he likes from a sea of brands, and you could declare with conviction the title of the film he’d appreciate for your Saturday night date – all good stuff.

Over time the uncertainty faded away as he showed up for you in all kinds of delicious ways. Like when he drove you 700 miles in a snowstorm to your grandmother’s funeral, the way he loves your dog even though he didn’t want one, and how what matters to you now matters to him. This is how a good life is meant to be, yes? Yes.

Except… here’s where we blow it:

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The Downward Spiral…

Tuesday, September 27, 2016

What’s a nice response to give when a guy has gotten a little passive aggressive because he read a question in your profile that says no thank you?

Why would you look for a nice response to give to a pansy ass resisting who you are and what you need? I’m not keen on adversarial behavior, so coming up with kind ways to reward someone who’s demonstrated behavior that’s resistant to who you are and unacceptable for a healthy partnership isn’t my strong suit.

My nicest response in this case would be none at all. Go live your life and surround yourself with people who are running towards you. Ones who if they need clarification or question your boundaries will do so directly, kindly, and with respect when asking you questions.

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WTF with the Disappearing Dude & Grieving Sucks

Friday, September 23, 2016

WTF? I started chatting with a great guy online. We texted, and I would hear from him several times throughout the day, exchanging pictures, stories, etc. He repeatedly stated how much he liked me and wanted to pursue a relationship.

We planned our first date but then, according to him, his son was hospitalized from an accident. I told him postponing our date wasn’t a problem. He continued to text regularly, telling me how much he liked me, and even stated that he no longer visited the dating website. This all seemed too good to be true. So I asked him if he was being completely honest and straight with me. He promised on his parents’ grave that he was. Anyway, this went on for over two weeks. Then suddenly he’s gone. No messages, no phone calls, nothing. What gives? If he wasn’t interested, why would he continue messaging me for so long? It seems cruel.

Dear WTF,

He was hit by a beer truck and has amnesia. No, wait, that’s not it. Did you say that one diabolical phrase that totally turned him off and made him run for the hills? Of course not. My guess? He wasn’t the man he said he was, and you were catfished.

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It’s OK to Judge & Detachment is Not a Relationship Style

Tuesday, September 20, 2016

What’s the best way to communicate that you’re not interested in dating outside your race just because it’s not your flavor of attraction?

If you’re an online dater, you can use the sorting filters they provide. This gives viewers information about your preferences but won’t block them from contacting you.

If someone who isn’t your type contacts you, it’s okay to say “no.” If you’re not feeling it because your suitor is of a different race, or twice your age, half your age, works full-time as a walking sandwich board, or has beady eyes, try this reply: “Thanks so much for reaching out! After reading your profile I can see we’re not quite a match. Good luck out there!” If they reach back to engage after that, use that key on the top right of your laptop labeled “delete.”

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Waiting & Porn #Annoying

Friday, September 16, 2016

What is the best way to deal with guys showing up late on a date or not at all? 

“Hey, you know what’s better than me waiting for you? You waiting for me!” Some daters really think this.

When a guy shows up late on a date, he’s telling you who he is, so listen up! Maybe he’s always late, a never-to-be-counted-on-slacker.  Maybe he’s overly optimistic about time. Or maybe something legitimate happened that was an unusual circumstance.  I’d hear him out from a place of curiosity instead of anger. Your first few dates are a trial period of getting to know each other, and if he’s late, that’s definitely something to know about him.

Before you set out on a date…

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How Can I Spot a Player?

Tuesday, September 13, 2016

What would be warning signs of a guy who is not ready to commit or a player? How can I spot a commitment-phobe? 

The real question here is what is he committing to? If he’s agreed to a date, he’s already committed to you. He’s committed to a date. You can’t expect more from a total stranger.

We want to know as soon as humanly possible if this person has staying power and the ability to commit to us, possibly for a lifetime. But trying to sort for that in the first few dates is like trying to predict who will get the final rose on “The Bachelor” on opening night of the season. I mean sure, there are some early and obvious candidates who are blowing it. You can wait for drunk girl, cuz you know she’ll show up in episode one. And keep an eye out for the slightly strange and inappropriate loudmouth. You can most def count on crazy-possessive stalker girl to lose that rose. The same can be said about a first date. If he’s a seduction scene creeper, it’s fine to belt out, “What up, player?” and be out. (And if you do this, please IPhone-record it and send it to me for my personal amusement.) For normal daters, it’s going to take some time.

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How Do I Get Past Dating Someone Overweight?

Friday, September 9, 2016

I’m a person who is fit. Health and exercise is really important to me. I’ve recently met someone who’s active but a bit overweight. How do I get past that if he seems to have everything else I’m looking for?

We humans want to be loved for exactly who we are and exactly who we are not. Maybe you get past the extra girth and maybe you don’t. You may need to find a person who’s as committed to fitness and health as you are — only you get to say. Speaking as a rotund person, I’m here to tell you it’s 100% acceptable for you to pass on this guy, and if you do, don’t be hard on yourself. You’re allowed to like what you like and have preferences.

There are specific areas of life we pay attention to. For example, I’ve plunged head-first into the area of dating, sex and relationships and I spend a ridiculous amount of time learning things, reading things, thinking about things, and discovering things in this realm. I don’t know jack shit about trigonometry, botany, or Celtic traditions. Also? I don’t put my time and attention on the types of food and exercise needed to not be a round person. I choose not to focus my time here and at the moment, I’m okay with this. Luckily for me, I chose a partner who can fully get behind all that I am (and all that I’m not).

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Is it Up to the Guy to Plan Dates?

Tuesday, September 6, 2016

Is it up to the guy to plan each date?

It’s up to the guy to plan each date — if you want him to.

The beginning of my 121 first-date dating adventure started after the end of a long-term marriage. At 35, one thing I knew for sure was I was looking for an alpha male. I’m an extremely self-reliant and opinionated person, so I was truly looking for partnership, but the flavor of guy I hoped to find was a type A, decisive, masculine man who was happy to take charge. This is by no stretch of the imagination every woman’s cup of bossy-pants tea.

What’s your flavor of partner? Do you want to run the show, trade off, or have someone take charge? If you want an alpha too, I recommend you let him lead.

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