Ask Wendy

Is It Too Late to Explore My Sexuality & Lifestyle Choices?

Friday, May 11, 2018
Hey Wendy,

At one point I saw myself as being married again, however, lately I’ve been thinking, do I really want that?

I have been reading and listening to talks about polyamory and soft swinging and it kinda has me intrigued. At this stage in my life, (in my sixties) is this even a good idea?

Most of the men I’m meeting on those dating sites have asked me about threesomes, both with another woman and with another man.

In the past, it’s not something I would have considered but for some reason, I am curious now.

How does a vibrant, healthy woman go about meeting people of like minds? I’d like to explore my sexuality in a non-judgmental way.

Sandy, Vancouver, B.C.

Hey Sandy,

Chapter 1—Exploring Sexuality at Your Age:

Is being in your sixties a good time to start exploring? Well, I’d say it’s a hell of a lot better than trying new things at twenty. I’m guessing that, at sixty-something, you’re confident, you know yourself, you’ve said the words “no thank you” a couple of times, have sharp discernment skills and possess very little need for shame—at least as compared to the twenty-year-old version of yourself. So, yes, now is an excellent time for you to explore anything that interests you. Sixties are the new thirties!


My Boyfriend Has Friendships with Other Women, Help!

Friday, May 4, 2018
Hey Wendy

I have been in a relationship with my boyfriend for 15 months. We have a lot going for us and we are both super attracted to one another.

He has quite a history with the ladies. He said he thinks that he slept with over 150 women, and he is 48 yrs. old.

Over time, I’ve discovered he has close to 50 ex-girlfriends and/or ex-lovers as Facebook friends. He’s close to four or five of his ex-girlfriends. He insists on having emotional ties to a variety of women and he insists on going out for drinks with some of them now and then, and I am not invited.

This is a major issue in our relationship, as I feel like he has so many ties with other women that it takes away from time and energy in our relationship together. He can be a shameless flirt at times, and I think he basically just loves attention.

I know that there is nothing I can do to change his past behavior, but my issue is with his present behavior and all of the attention seeking from women, and the women posting comments for him on Facebook and elsewhere. Though he isn't doing this too often, he refuses to give up spending time alone with exes.

Is this situation doomed, or is there a way that I can relax and be alright and feel safe with him?

CC - Washington D.C.

Hey CC,

I’m sorry your boyfriend’s entanglements have gotten your hackles up, and I get it. The continued presence of these ladies in his life must make you feel like your situation is volatile and unsafe. And you’re right—he’s not going to change. He may curb some behaviors for you (and potentially resent you for that), but fundamentally, he won’t change.


Is a Guy Gay If He Wants Anal Play?

Friday, April 27, 2018
Hey Wendy,

Does it mean a guy has bisexual tendencies if he mentions he wants anal play?

I'm getting to know this guy; we were fooling around, and he mentioned he wanted a certain type of movement from me as we were dry humping and I was in the more masculine position. When I didn't understand, he explained, "You know, like if you had a dildo and were f---ing me."

I'm not sure what to think. I mean, if I had met him online, I could see that he considers himself straight or bi or bi-curious or whatever, but since I met him IRL, I don't have any of that info upfront. How could I bring this up to get more clarity from him?

I'm not sure how I feel about screwing a guy with a dildo. And I can't really see myself with a bisexual man, if that's what it comes down to. It might be a deal-breaker. Anything else I should consider that I'm not seeing yet? Thanks.


Hey Zoe,

Pegging! The sex act of fucking a guy with a dildo is called pegging. And it’s not just for bisexual men—it’s for anyone! Straight guys, gay guys, bi guys, the ladies, trans, cis, and gender-fluid folks, too. I suppose the only group of guys that pegging is not for is asexual guys—oh, and also guys who don’t want anything stuck up their asses, regardless of orientation.


Why Do Men Disappear Before We Even Meet?

Friday, April 20, 2017
Hey Wendy,

I am having difficulties on why men disappear. I am online dating, and we exchange numbers, talk for a little, then they disappear. I touch base with them the next day, I hear nothing. So frustrating!!!

Please help! I am so sick of men disappearing on me. Any suggestions?!?

Liz D – Albany, New York

Hey Liz,

Yes, I do have a suggestion. Don’t talk to them before you meet.

Wait, what? Am I crazy? No.


What’s the Etiquette For Paying For Dates?

Friday, April 13, 2018
Hey Wendy,

I used to have a hard time letting guys pay for me and take me out. I used to attract men who wanted me to go Dutch, or even pay for them. This was a turn off for me. I’m a successful and independent woman and I don’t need men to pay for me, but it does feel really good. It puts me in the feminine. I enjoy it.

I’m dating a great guy who is used to women splitting the check but will pick up the tab, as I’ve expressed that I like being taken out. But I have this nagging unpleasant feeling inside of me when he does. I feel guilty or as though I’m a “gold digger.” I’m still not quite used to this. (I have taken him out to dinner once and will get him small gifts).

Does the guy always pay?

I would love to hear your thoughts about money matters while dating. It is so confusing to me.

Monisha L. – New York, New York

Hey Monisha!

First, congratulations on graduating from dudes who don’t pay and/or expect you to pick up the tab. Girl, that is not okay. Say it out loud with me: “I don’t pay for men on first dates. Never again.”

Here’s the deal with paying for dates:


My Boyfriend Still Lives with His Ex

Friday, April 6, 2018
Hi Wendy,

I am a 59-year-old woman dating a 65-year-old man. He is kind, considerate, good looking (in my eyes), healthy, financially responsible, and romantic. We’re exclusive, we’ve traveled together, and he tells me he loves me and wants to have a future with me. He is respectful to my kids and my friends. Feels like a dream relationship...I am very happy with him...if I don't allow myself to think about a complication in his life…

8 years ago, right after his divorce, he got involved with a woman who moved in with him. After a few years, she moved out. Six months later, feeling lonely, he asked her to move back in. She said in order for her to move back in he had to agree to put her name on the deed of his house. He complied because he wanted her back.

They broke up a year ago. He asked her to move out and offered her $140,000. She refused, saying he needed to give her "a lot more than that." A lawsuit has been going and she refuses to leave.

He has been honest with me about all of this from the beginning after a few dates. I decided to continue to see him since he seems trustworthy and we all make mistakes. He feels bad that he has baggage and he is doing all he can to get this problem resolved. The problem is she is still living in his house! They have a court date in June.

Is it normal for me to feel uncertain since I have a fear of abandonment? Any advice for me?

Jasmine Y – Phoenix, AZ

Hi Jasmine,

Another woman under his roof is disconcerting, and I can see how it would cause uncertainty in your relationship. If the romantic part of their relationship is over (and it sounds like that’s long gone), then I think that, if you are willing to hang in there a minute, this situation just might right itself.

We all have varying amounts of baggage. And his comes in the form of a cantankerous ex-girlfriend. Too large to slide under the seat or stuff in the overhead, that’s for sure. And the lid isn’t all the way closed on this one yet, either.


My Boyfriend Looks at Other Women, Help!

Friday, March 30, 2018
Hey Wendy,

I've been dating a guy for a couple months. He tells me he loves me and wants a future with me. I enjoy him, and we’ve shared some wonderful times. But I've noticed some actions that concern me:

1. When an attractive woman (waitress or patron) is near us in a restaurant, he'll attempt to make eye contact with her and strike up a conversation with her. He will continue to keep a furtive eye on her through the meal while he sits and talks with me.

2. He scans a room looking at other women wherever we go. Once, he turned around to check out a woman and almost tripped down some steps.

3. He was showing me some pics of us on his phone and flipped through a number of photos of women, some almost in the nude, and explained that these were photos of models he subscribed to on social media.

4. He admits he is a highly sexual person and has been so since he was a very tender age.

5. He has had multiple one-night-stand encounters and a number of relationships. I have a feeling he has had more than he has admitted to me.

6, In his most recent relationship, while he was still with her, he started looking to date other women before he officially ended that relationship. To me, I consider that cheating.

This is quite disturbing to me and it's a huge discrepancy that I have a hard time reconciling. I told him if there is no fidelity in the relationship, then it's not something I want. He asked me to trust him, that he is capable of change and fidelity, but I'm not feeling confident about that based on these items I've discovered. Should I trust him?

Ann T. – Dubuque, IA

Hey Ann,

Should you trust him? Absolutely! You should trust him for what he has a track record for. Based on that track record, you can 100% count on him to: (more…)

How Do I Stop Attracting Jerks?

Friday, March 23, 2018
Hi Wendy,

For 25 years, I was married to a physically and verbally abusive man. I was going to file for divorce, but became seriously ill, and took him back as I had no one else to care for me. When I recovered when he got terminal cancer and reacted with anger directed at me. I ended up caring for him until he died. Yet, even in the last week of his life, he threatened to kill me. I feel the only way I could ever get out of that scary marriage was through his death, tragic as it was.

About a year after he died I went on several dates, 3 with men I knew and 2 with men I met online. One guy was completely rude to me. If I’d known better, I would have gotten up and left. The other four directly propositioned me for sex on the first (and last) date, two of them grabbed me and kissed me, one squeezed my butt. I was shocked. I stopped dating after that.

It’s been three years and I know there must be decent, respectful men out there. But given my scary marriage, and the bad behavior of the first few dates I tried, how do I feel safe with a man again?

Karen S – New York, NY

Hi Karen,

I’m so sorry you’ve had such a rough go of relationships, and I’m glad you are out of the nightmare of your 25-year marriage. My God, that sounds scary!

I have some not-so-great news for you. I don’t recommend you date. Seriously.


Do I Have To Have The “We’re Dating Exclusively” Conversation Yet?

Friday, March 16, 2018
Hey Wendy,

I am newly single again and I remember from 20 years ago what my process was for dating. As soon as I met someone that I liked, I saw them exclusively and just worked through things. And ultimately, never identified what I needed. Been there, done that!

Now I’m older and wiser, and I want to date around until I’m absolutely sure that the person is someone who has long-term potential (and after 20 years of marriage, I am in no great rush!). That being said, when and how does the “we are just casual” conversation come up? Or it doesn’t have to?

I’m a month into dating this guy and as much as I enjoy him, it’s way too early to know if he has good long-term potential. My thought was to just enjoy our time together, continue to see other people, and not bring up the fact that we are casual and seeing other people at this point. I think it would actually crush his unspoken, but obvious, a fantasy of him being the only apple of my eye. If he asks me if I am seeing other people, which I can’t see this guy doing, then I will be upfront with him. But otherwise, until he brings it up, I wasn’t going to bring it up. I realize I am possibly sending mixed signals because there are a lot of sleepovers and I always find time to see him, so why would he think I’m still seeing others? Is that his bad for assuming or my bad for not spelling things out for him?

Ella P. – San Diego, CA

Hey Ella,

Thanks for this question. Thousands of daters find themselves in this situation. This oh-so-common conundrum is caused by the framework our society has built around dating, and it’s a bit, well, fucked up, to be blunt. So, let’s reframe this problem, okay?


What Happened in My Relationship? Was it Him or Me?

Friday, March 9, 2018
Hey Wendy,

A little over two months ago, a guy I went to high school with reached out to me on social media. We had always had a thing for each other, but we never acted on it up until now. We exchanged numbers and started texting, FaceTiming and Snapchatting constantly.

We lived in different states at the time, so it was difficult to see each other in person, but I did go see him a couple of times and would spend a few days with him each time. Every time we were together it was great, we had a lot of fun, and he made me feel special. He told me that he was serious about me, that he could see a future with me.

We did talk about the long-distance thing hindering the relationship, and so about a month and a half later I moved two hours away.

I had an extended stay with him recently. After a few days, I started to notice a change in him: he was distant and less affectionate. When I asked him about it, he said everything was fine and within a few days things seemed to be back to normal.

When I returned home, he seemed distant. I texted him and only got brief responses. I tried to FaceTime and got no answer. Finally, I texted and asked him if he was going to tell me what was wrong. No response. He ghosted me.

Meanwhile, he was still the first to look at my social media. I asked him to be an adult and tell me what happened. His response was, "I just have a bad feeling. It's not going to work." I asked him to explain and he just said, "It's just not going to work." That day he deleted me from Snapchat. What does that mean??? Was it me, was it him? Please help!! :/

Jessie T, Kansas City, MO

Hey Jessie,

Oh my God, I’m so sorry, you uprooted your life to get dumped! And if you’re still standing over there in shock wondering what the hell happened, I hate to be the bearer of bad news but yeah, that’s what just happened here.

You know, people always get so flustered with me when they hear me say “long-distance isn’t real,” but I stand by my belief. Are there times that a long-distance connection can turn into a real and lasting relationship? Of course! But there’s a whole lot of real that has to happen in between to get to that happily ever after.


What’s the Right Pace for Dating a New Person?

Friday, March 2, 2018
Hey Wendy,

I met a guy at a Meetup who asked for my number and, on our first date, brought a list of really fun questions that helped break the ice. Come to find out, when I mentioned some specific ones to my girlfriend, she told me they're the famous 36 questions that lead to love. These questions start innocently enough and become increasingly intense and probing until you're baring your tender little soul, and you have no idea how you got here! The frog has been boiled!

We've been on a medium-length first date and a lengthy second date, and had two lengthy phone convos and still haven't finished all the questions. We always end up going off on tangents and talking about a million other things.

Even though these questions are new to me, and I've never gotten close to someone in quite this way, it seems like I have been burned before, getting too intimate, too early. And even though I would never have picked him, and I had low expectations of our first date, I like this guy. He makes me feel safe and special, and he turns me on. This feeling, too, is familiar to me. Some people advise going slowly while getting to know someone. That's never really worked for me. I tend to develop intense feelings quite swiftly, and if I stay too long in the getting-to-know-you phase before forging ahead into romantic possibility, one of us inevitably Friend Zones the other, and then it's game over, and it all feels like a waste of time.

So, my question is: do you have any thoughts about this? Should I be more cautious? (The very question makes me shudder, as it feels so inauthentic to me.) Should I be this open, vulnerable, and forthcoming this early?

Anna P., Austin, TX

Hey Anna,

Ok, so first off, thanks for providing the readers and me with this inspired list we’ve all heard so damn much about! And I read it to see just exactly how hot that water got for little froggie.

Verdict: I love, love, love these questions! I also love any guy who brings them to a date. It’s a tell about him; he’s interested in knowing you and willing to go deep.

But don’t let my opinion sway your own gut instincts or your process.


Should My Marriage Be Open Or Closed?

Friday, February 23, 2018
Hey Wendy,

I've been married to my wife for nearly 20 years. About five years ago we made the decision to open the marriage, and while I think the decision has been great, lately we've run into some complications.

What underlies our arrangement is that she has been losing interest in sex in general. She's going through menopause and is on antidepressants (which doesn't help). With the open marriage I got the sexual connections I craved while she was alleviated the burden of being the sole source of my sexual attention. It worked well for both of us.

The challenge is that my wife is now having second thoughts. She's thinking she might not be as amenable to the open marriage as she originally thought. She tells me she did it because she feels I'm a good guy and I should have what I want. But she's no longer sure it's what she wants.

In fact, it's starting to cause marital trouble. Which leads me to my question.

I'd prefer to keep the marriage intact if possible. We're best friends and good co-parents, and I'd like to grow old and die with her. On the other hand, the past five years have made me realize how much I value an open relationship. I treasure the wonderful web of delicious and close connections I've made and don't want to give them up for the world.

But she's not sure she can live with it anymore. I could keep the marriage together if I agree to close it again. Or risk losing it if I dig in my heels and insist on keeping it open. Hence my conundrum.

While I have my own opinion of what I should do, I would love to hear what you advise.


Kevin T. Belvedere, California

Hey Kevin,

Conundrum. Yup, that’s what you’ve got there. What a tough spot! Being trapped between your love for her and the need for the wonderful web of connections you’ve cultivated through your open marriage isn’t an easy place to be. I sure wish I could tell you how to keep your marriage open and have her be fine with it in 140 characters or less, but sadly, I can’t.

Here’s what I will say, though: I’m pulling for you two to figure out a creative solution that works for both of you—a solution in which everyone gets “enough” of what they need. For the two of you to be in a healthy, happy marriage that will continue to last, you each need to do your part in sorting this out.


Can I Date Someone With A Filthy House?

Friday, February 16, 2018
Aarg! Help, Wendy!

I've been on a couple dates with this guy, and when he invited me back to his apartment, I said yes. He's artistic and musical and a programmer and a guy, all of which is to say that his place was kind of a wreck. I have my own clutter. It wasn't the clutter that bugged me, and I thought I was okay with it...until I used his bathroom. It was so gross! It looked like it had never been cleaned, and I couldn't imagine taking my shoes off. It grossed me out, made me feel unsafe (health-wise), and made me feel completely unspecial. The visit to his place was very spur of the moment, so part of me wonders if he would have cleaned up if he planned in advance to have me over. Is having a clean apartment something I could reasonably expect him to do for me? How do I have a convo about how much his mess depletes me and makes me not want to get physical with him?

June L. Houston, TX

Hey June!

So, I cohabitate with someone who’s artistic, musical, in tech, and also a guy, but he manages to keep a bathroom pretty damned tidy and definitely clean enough to walk into with bare feet, so let’s not let these characteristics be your dude’s “good reason” for living in filth. Housekeeping standards vary drastically from person to person, but if we were to generalize, statistically speaking, straight guys don’t pay as much attention or put the level of detail and effort into cleanliness as we do. This doesn’t make being a slob okay, though.


How Does #metoo Apply to Me?

Friday, February 9, 2018
Hey Wendy,

#metoo is really hot right now. I don’t think it’s ever happened to me. Am I being oblivious? Am I too unattractive to be sexually harassed? Men have been inappropriate, sure, but I don’t think that’s assault. Am I missing something?

Stephanie T, Chico, CA

Hey Stephanie,

Like any large movement, there’s a million different voices to and definitions of what #metoo means. Whatever it means to you personally (or not), I’m thinking you can count yourself lucky to feel like a bystander on this one.


Is it Disrespectful that My Husband Doesn’t Wear a Wedding Ring?

Friday, February 2, 2018
My husband doesn’t wear a wedding ring. I think people notice, and I don’t really want women hitting on him. For me, my wedding ring is a reminder of our love. Is it disrespectful? I’m not sure how should I feel about this…

Tanzie, Atlanta, GA

Hey Tanzie,

There are gazillions of other advice-slingers out there who’ll disagree with me, so if you need a different answer than mine, one should be easy to obtain. But before you run off asking, my thoughts, while they may not be the kind you want to hear, will give you the most personal power, freedom, and peace if you can embrace my point of view. So, let’s get started addressing your concerns:

People will notice: Yup, some will. What does that have to do with you and your life and bond with your husband? People also notice those shoes you’re wearing, and they’ll pass judgment on them, too. People are extremely judgy, have you noticed? (more…)

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