Ask Wendy

How Can I Tell If We’re Compatible to Couple?

Tuesday, November 7, 2017
Hey Wendy!

I’m dating a 50-year-old, and I’m in my early 40’s. I’m wondering, how can I tell if we’re compatible and if we’ll have fun together? He drinks some, and I don’t drink. I’m a trail runner, he’s a street runner (marathons). It seems like we don’t have a lot of activities in common. So how do you know?

SS – Charleston, SC

Ask Wendy explores if these two are compatible to couple.


Dear S,

While having activities (outdoor or otherwise) in common is preferred, it’s not required for a happy life together. I’m assuming you like trail running solo or you have running buddies already, right?

It really does take a village to get all our needs met to be a well-rounded, happy person. And those who lean on their partners for everything are usually much worse off than those who have a healthy network of friends and loved ones to help get the job done.


My Boyfriend’s Heath Problems Are Alarming – Can I Get Him To Change?

Friday, November 3, 2017
I met my boyfriend online. He is a great boyfriend and is very attentive. My only concern about him is his health. He drinks a lot with his friends once or twice a week, has high blood pressure, and currently has ED.

His high blood pressure is genetic. He is thin. I’m just frustrated that he is not going to see his doctor to get everything figured out and make whatever changes are needed. I’ve read that drinking alcohol alone can cause ED. His first response was to quit taking his anxiety and high blood pressure medication for a week to see what was causing his ED. I encouraged him to see my wellness doctor and his best friend encouraged him to also see a doctor and not go cold turkey from his medicine.

He also said he would go to yoga with me and would start eating better. He is eating better. I’ll invite him to join me for yoga on Sunday. I’m guessing he has low testosterone and that the alcohol and possibly his blood pressure med are factors. He is 47. My ex-boyfriend also had some ED issues and didn’t take good care of himself until after we broke up. I don’t want to go through all that again, and I don’t want to be a nag or his mother.

EE – Dallas

Hiya EE,

What I see here is a common theme amongst the sisterhood. We say, “yes” to a relationship with the cute catch standing in front of us without saying “yes” to the whole package as-is. We say “yes” to a relationship, but what we really mean is, “Yes, I want to be with you…right after I get done fixing you.” This doesn’t go over well with men, and as you’ve seen from your past, trying to change a man often doesn’t turn out well.


How Can I Tell If a Relationship is a Bad One?

Tuesday, October 31, 2017
Hey Wendy,

I’m just going to lay it out for you. I’m 28, I’ve had two failed marriages with cheating, beating, and verbal abuse. The two relationships that followed were ones where I was safe, but still cheated on.

Suffice it to say I feel I make bad choices in men. So, my fear is with my new relationship forming (we're currently taking it slow and building on friendship and then upward, which is new to me) that I made another bad choice.

I never see the flags until months in, after I've poured my heart into it. So, what should I watch for early on? What are the red flags?

WF – Washington D.C.

Dear W,

I’m sorry you’ve had to endure abuse. And I’m happy to hear that your past is in the past and that you’re taking it slow and becoming friends first with the new one.

The first thing you can do to see if he’s a good guy is to have a another guy in your life (like a brother, mentor, or friend) meet him — and soon.


Can I Date My Friend’s Ex?

Reprinted from April 21, 2017
Hi Wendy,
I’m on an online dating site, and I recently connected with a good-looking guy with a great profile who looked familiar to me. I messaged him to tell him he looked familiar, thinking maybe we went to college together or something. He messaged me back, we couldn’t figure out how we knew each other, but we kept chatting and we get along well. Then it dawns on me, he is the ex-husband of an old friend of mine. This friend and I used to be close to years ago. But I haven’t spoken to her in about 7 years. We are Facebook friends, but don’t even communicate on there. Back when they were married, I didn’t know him, I’d never even met him or heard anything about him. He wants to get together for dinner or drinks and see if we connect in person. I am very interested in getting to know him better but not sure what to do. She recently moved out of state to live with her boyfriend of about a year. Do I go or not go? Do I tell her first or wait and see if he and I like each other?

Dear Dater,

Let me get this straight: You want to know if it’s okay to go out with a guy who used to know someone you used to know, but neither of you are in contact with her anymore? A friend whom you no longer talk to, who lives out (more…)

How Can I Deal with His Financial Problems?

Friday, October 27, 2017
Hey Wendy,

My boyfriend is having financial problems, serious problems. He won’t accept any support from anyone. I feel he doesn't want me to feel he cannot provide, but for me it’s not the money, it’s the feeling of having a partner. He is always worried, unhappy, confused, not with me and when I try to pay a bill he gets so angry and we fight.

We don't go out because he can’t afford to and he won't accept me to pay for things like movie tickets or dinner or etc... If he doesn't accept any kind of support or even to sit with someone who can guide him on what to do, we are getting nowhere.

I feel distant from him, and this is effecting our relationship a lot. I don't know what to do. I was open and honest, he knows I can help a bit financially until he is back on his feet. Help please!

CS – Dubai

Boyfriend’s financial problems cause strife in relationship.

Dear C,

It may feel like you have one problem, but you have two. The first is your boyfriend’s financial problems, which may come and go throughout your lifetime as they do for almost all of us. The second, however, is an even bigger problem, and that’s the fact that someone you love won’t receive from you. What’s with that? What happens on his birthday, no presents?


Can I Invite My Friend & Not Her Boyfriend?

Reprinted from April 14, 2017
Hi Wendy,
A bunch of my friends want to get together Saturday since everyone will be home for Easter.My friend, Allison is dating a guy who we all dislike. He's about 10 years older than her, and the two of them got in a fight in front of us the first time we met him.

My friend, Kate is asking if she should ask Allison to not bring her boyfriend. This is most likely going to be a problem because Allison will want our friends from out of town to meet him. As much as I don't want him there I’m bringing my partner along (everybody loves him) and I'd feel bad if he came but her new guy couldn't.

Dear Torn,

“I’d feel bad if he came but her new guy couldn’t.” Yeah, that would be kind of a dick move, and will only cause strife between friends. Look, if it were a ladies’ brunch, you’d have a leg to sand on, but it’s not. This is friends getting together to hang out. She gets to bring her new boyfriend. You get to do one of two things:

Choice A) Put yourself at the other end of the table from them so you don’t have to deal with this loser, or…


How Do I Get A Commitment After Sex?

Reprinted from April 7, 2017
Hi Wendy,

I put myself back in the world of online dating at the start of this year. I’ve been dating a lot of different guys, but there’s one that’s a standout. We’ve had 6 dates now, but I’m still dating others. This guy seems to really like me. He’s mentioned me to important people in his life, and he wants to take me to the family cabin in Tahoe.

Here’s my question: I really like him and don’t particularly want to date other guys. I want him to lead the direction of this relationship but he hasn’t asked me about being exclusive. What do I do? Do I discontinue dating other men but not tell him, or do I let him know that I won’t be sexually active with him anymore until we agree to be exclusive? Or how does this thing work?

Dear Dater,

So far this sounds promising, congratulations! This exclusivity thing is not an uncommon problem; it plagues women from around the globe. I’d say this: If you want him to lead the direction of this relationship, then let him lead. I’m always a fan of that, because if he’s leading, then you can see where he’s leading you to—down a path to a happy life together, or straight into a ditch. Letting him lead also allows for the space to show if he’s going to put those words into actions; it’s a way to gather data that will help you determine if this potential relationship has legs to stand on.


Where Are All the Single Guys Over 50?

Reprinted from March 24, 2017
Dear Wendy,
You say there are plenty of quality men available to date; even for us women who are over 50. But I'm not seeing them... anywhere!
True, I don't live in a highly populated area, but even online there are very few men in my search area. And I've expanded my search to 3 hours’ drive away.
The closest I've even come to dating is with a lovely man who lives 8 hours away. After 6 weeks of phone calls, he admitted he’s unable to be in a relationship with anyone.
Please, give me some hope for the future!

I will absolutely give you hope…if you’re willing to shake things up a bit. Because you’ve already learned an important lesson: You aren’t finding men where you’ve been looking.

Can’t find them on a dating site? Try a different dating site. Or five.

Can’t find them in your town? Maybe it’s time to relocate.

Moving is hard—believe me, I get it. I loved living in the idyllic town of Sonoma, California. I’d made friends, chosen family, and for twelve years I ran an accommodations business that I built with my own bare hands, and the name of that company? Stay Sonoma. From the looks of things, I had to stay—but I didn’t.

I weighed what was most important to me at that point in my life: having a partner, or owning a local business in a country town surrounded by friends. I decided to move to Oakland; nowhere near as pretty, serene, or fancy, but do you know what Oakland had that Sonoma didn’t? Single men!

You can stay where you are and keep trying, and it may happen for you. Your odds of importing someone are pretty slim (unless you live on Maui), and long distance has the drawback of attracting those not able to fully commit, as you seem to have already discovered.

What you’re really left with is this: Are you going to try a different site or different town, or are you going to own your choice to stick with the current method and the consequences that come with it? There is no wrong answer here, but yes, I am nudging you to empower yourself and to tell the truth about the situation instead of falling victim to your own circumstances.

I do promise that there are lots of great guys over 50 out there who are single and available. But the old fairytale “someday, my prince will come” may not apply here. You may have to go to them, because they’re probably not going to come knocking on your small-town door.

Good luck!

Why Won’t She Take a Complement?

Reprinted from March 17, 2017
I’ve been dating my girlfriend for about six weeks now. And she does this thing; she denies any compliments I give to her. When I turned 30 I realized I was bi and this is my first real girl/girl relationship, so that might have something to do with it. The guys I’ve dated didn’t do this. Advice please?

Easy. The next time you say, “That top looks amazing on you” and she says, “No it doesn’t,” or you say, “You’re so smart!” and she says, “No I’m not,” take her by the hand, sit her down, and say, “Look, I know your inner (more…)

I Make More Than My Husband, Does That Matter?

Reprinted from March 10, 2017
I’m a resident physician about to start my first real doctor job this summer. My husband is a teacher and his income will not change. Because of my debt and higher living expenses, our take-home pay is about the same, so in my mind, if I can afford something, so can he. Throughout the course of our marriage, money situations have been pretty typical; we have split the cost of vacations and special leisure events, but he pays for meals most of the time.
We have different priorities around how we spend money. And I'm literally going to be making 4x more than him in just a few months. I can’t imagine what it would be like if I bought us both airline tickets for vacation. Is that emasculating or insulting? I have the idea that it's my money, so I should be able to spend it (on him) if I like, but I also don't want to be an Alpha Female. I'd like some input on how to handle everyday situations like this.

Hey Doc,

First off, congratulations on your job!

Do you have separate accounts now? It seems like you might from your comment, “It’s my money.” If you have different priorities around money, I recommend you keep your accounts separate, but create a joint account for household expenses and shared investments.


Do I Need to Lose Weight to Date?

Reprinted from March 3, 2017
Hey Wendy,

So I’m overweight but have lost 8 pounds in the last month. Do I need to lose weight before I date? I conducted a social experiment by creating two different Tinder accounts: the first using photos of me at my old weight, and the second with photos of a woman who looks a lot like I will when I lose about 20 pounds.

I swiped right 100 times. Real me got zero matches. Fake, future me got 9 guys.

I am going to lose 20 more pounds. It will take me about 10 weeks of hard work, but I’m committed. I am considering using my real photos, but with the help of Photoshop to show what I will look like soon, to try to go on dates. If I get busted, I can just say the shots are a little old and I’ve gained some weight. Since Tinder is 100% based on looks, I feel like this is my only option.

Bella K. - Los Angeles, CA


Girl, no. This is a terrible plan, and not your only option. You do not need to lose weight before dating. Do you think when “real you” gets there not looking like her online photos that your date is just going to be cool with it? Trust me on this one, I assure you, he will be far from cool with it and your evening will not go well – at all – not even a little bit.

Is it Love if There Isn’t a Spark?

Reprinted from February 24, 2017
I’ve been dating my boyfriend for a little over a year. He's thoughtful, has a great sense of humor and is overall really good to me. But having been in a few long-term relationships, there's not the fireworks I’m used to with this guy. I really care about him, but deep down I’m just not sure. I don’t want to hurt him.
My other relationships have been intense. I was deeply in love with equally painful break ups. That deep "I would move mountains for this person" feeling is the emotion I'm fixating on here. I just don't have that for my current boyfriend. I’m not sure what to do.

Have you ever been to a Fourth of July fireworks show that never ends? Yeah, me neither. Fireworks in any relationship fade over time. However, that dimming of the flash and bang is replaced with a delicious sense of belonging and knowing when you’ve hit upon a keeper, so it’s kind of a trade. You can always reignite the fire and crank up the heat again when you’re intentional and creative about it. But that magic spark doesn’t just (more…)

What Does “I Can’t Give You What You Need” Mean?

Reprinted from February 10, 2016
Hey Wendy,
If a man you were dating said to you he can’t give you what you are after, but you don't think he really knows what you want, how would you go about addressing this with him?

I would say, “Hey. So what is it that you think I want?” Then I’d listen. I’d clarify. Most of all, I wouldn’t pull any punches with this guy since I’d know in my heart of hearts I had very little to lose. Usually when a man says this, he actually means, “You want me to love and commit to you, and I’m not going to do either of those things.”

How Do I Handle an Unsatisfying Sex Life?

Tuesday, October 10, 2017
Hey Wendy!

I received this text from my boyfriend today.

“Is having multiple sexual partners a requirement for you in our relationship?”

My short answer is no. The longer answer is that I would like to try it to see if it could be a way to get my needs met and not lose this awesome guy that checks off all the other boxes.

This comes because in the last year he has not often been able to satisfy me sexually. I'm also interested in the BDSM lifestyle but relatively inexperienced. The lifestyle is not his thing at all. We have talked about this subject, seen a counselor, done some education and our sex life has improved but it's not where it needs to be.

I asked that we have the conversation in person when neither of us is tired or hungry. Text is a poor medium for us and creates misunderstandings. I would welcome your advice and input.

LN – Dallas, TX

Hey L,

I’d start this conversation with your boyfriend by asking, “Hey, so about what you said in your text, is that a real option for us?” because the two data points about your sex life that stick out to me are “it’s not where it needs to be” and how BDSM is “not his thing”. Based on what you’ve expressed in your question, it sounds like you’d basically be denying your own sexual needs by staying in a relationship with just him, and girl, I’ve seen it over and over—that never works out well.


How Can I Get Her Back?

Reprinted from February 3, 2017
Hey Wendy,
I met a woman online in November. After going on a few dates I asked her to be my girlfriend. She’s amazing, beautiful, funny, and always likes to talk. I liked that because I'm kind of socially awkward and it's hard for me to carry a conversation.
I had a bunch of crazy stuff happen over the holidays—extended family drama, started a new job, stuff like that. Our schedules didn't mesh well, so we saw each other maybe once a week.
She broke up with me and said that she wasn't happy with herself long before we got together. She hoped getting into a relationship would help, but it didn’t.
I ordered her roses and chocolate covered strawberries to be delivered on Valentines Day. What more can I do?

It’s probably really hard to see this right now, but there is someone out there who really wants to be with you—and you’re depriving her of this chance because you’re buying roses and chocolate-covered strawberries for someone who doesn’t want to be with you.