Ask Wendy

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.

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.

How Do I Break Up with a Friend with Benefits?

October 6, 2017

I'm in an open marriage. When my wife and I made this decision about five years ago, I would say it was one of the best moves we've made, and we are very happy with it. I've been fortunate to have made a number of friends-with-benefits relationships during that time, all with lovely, wonderful women.

My question to you is how to end an FWB relationship? I've found that for some of these relationships I'm now less sexually attracted to my partner than when I first started seeing her, and that I'd like to move on.

This makes me feel more than a little awkward, though. If we were in a serious, romantic relationship then a "true" breakup would of course be in order. But many of my FWBs I see only occasionally, as schedules allow, and by definition they are casual relationships. I've been very up front with my intentions with each, and I believe they share the same goals out of our relationship that I do. 

I feel really horrible on some level conveying the message "I'm not attracted to you anymore." That feels unnecessarily cruel. On the other hand, I don't want to just disappear and stop calling. I do feel my friends deserve the respect of having an open, honest conversation. And I genuinely like each of my FWBs; generally speaking, I'd like to remain friends with them. Just not necessarily with the benefits.

How would you suggest I handle one of these FWB breakups?

SR – San Francisco

Hey S,

Well done! Living outside today’s cultural norms to do what truly works for you and your wife is a brave move. I love you for that. I also appreciate how thoughtful and respectful you’re being to your lovers. Kudos. And by definition, a FWB relationship is designed to end—otherwise, these women would be considered your partners, i.e. polyamory. So I agree, it’s tricky.


When Is the Right Time to Tell Him About My Bipolar Disorder?

Reprinted From January 27, 2017
Sadly, I was diagnosed with bipolar disorder when I was 27—possibly as a result of several emotionally traumatic events. I’m in my mid-forties, I’m stable, compliant with medication, and have held down my current corporate management job for over 12 years. My colleagues don't know about my condition. My family and close friends do.
When is the right time to tell a prospective partner about my condition? The person I’m seeing lives long-distance. Is it better to get it out there, and if so, when? Before intimacy, after the first time one of us travels [to meet the other]? I would feel deceitful if I let it go too long, but I know there's no avoiding the conversation. What do you think?

Long distance or local, this isn’t something you need to roll out on a first date. You get to share personal information when you’re comfortable and feel safe with this person. I’d say wait until they no longer feel like a stranger to you and they’re someone you have an intimate connection with, but before you have sex with them.


Am I the Rebound?

Reprinted from February 17, 2016
I am starting to get the feeling I will be the rebound for the man I am dating right now. Do I stay or go?

Dear rebound girl,

I’m sorry! And good job catching this early instead of trying to convince yourself otherwise. We’re usually not eyes-wide-open about this stuff.

So…should you stay or should you go? This question is not for me—it’s for you. You know you can move on to what’s next if need be; that’s a given. But can you stay and have something mutually beneficial and life enriching with him? Can you afford to take the hit to your heart, give up the time on your calendar, and put your energy into him instead of someone else who really wants to stick around?A few of my 121 first dates were rebounding so I’ve had the experience of both walking and staying, and I didn’t regret either, but each were intentional decisions.


What’s the Differences Between Girlfriend Privileges & Wife Privileges?

Tuesday, October 3, 2017
Hey Wendy,

What do you consider are the differences between girlfriend privileges and wife privileges?

I love my boyfriend, but I’m wondering what privileges I should be reserving for when he’s my husband. At what point are you overextending yourself as a girlfriend? Like, would you do his laundry? Cook for him? Try anal? Cook in lingerie for him?

Would you do all this for a boyfriend? Or would you save it for marriage?

HW, Redwood City, CA

Hey H,

Are you asking me if I take it up the ass? Yeah, I’m not answering that. I will tell you, as someone who has no plans to ever marry my beloved partner of nearly five years, the one who I will most likely live with until one of us croaks, but is not my husband – he still gets all the “wifey” privileges I wish to give, and he has received wife privileges since we moved in together four years ago.


Dating A Guy With A Girlfriend?

Reprinted from January 20, 2016
I met a guy and we are falling in love/lust. He lives with his girlfriend and I would normally never do this. But we have crazy chemistry and we are attracted to each other physically, mentally, spiritually, and sexually.
Even if he breaks up with her (which he doesn't want to do) this can never end well, correct?
We have only seen each other three times, including when we met. I don't know what to do. He is amazing. Super hot, intellectual, meditates, is sporty, thoughtful, artistic, and all kinds of awesome. And he makes me feel cherished and safe. Help!

I’m missing important details from your question here. Is this new guy in a monogamous relationship and is cheating on his girlfriend, or are they in an open relationship? Because if they’re committed to a non-monogamous relationship, that may leave plenty of room for you, and it could end quite well. Also helpful to know would be this: Are you okay with him having a girlfriend, or are you looking for monogamy yourself?

Am I In Charge of Planning This Stupid Party?

Friday, September 29, 2017
Hey Wendy,

My fiancé is turning 50 in two weeks. We’ve had a tough relationship and his parents are cordial to me, but not nice. For example, his father recently hired a criminal lawyer to research whether I was trying to get his son in trouble, because my fiancé was arrested a while back due to his temper and I nearly had to have a restraining order. I was not physically hurt but his anger sometimes scares me.

His mother texted me today and asked what we are doing for his birthday. She is asking me to throw a big party, cater it and invite his friends. His friends apparently hate me too because when we had our issues, he told them personal things about me that were private. I really don't want to invite these people. I invited his kids and even offered to pay for his son to fly in. But I don't want this big party. It's going to turn my stomach knowing that they all hate me while I stand there and smile.

I suggested a weekend trip and he said no. The reasons he gave were he wanted to be at home with his family and friends for his birthday, and he didn’t trust me enough to travel with me right now.

I don’t know what to do. How would you handle this?

BT – Charlotte, NC

Hey BT,

Nowhere is it written that at 50 you are guaranteed a large-scale birthday party planned by your beloved. If that’s the way your fiancé wants to spend his 50th? Awesome. He can plan it and make it all happen, just as he wishes.


How can you get over loneliness when you’re single?

Tuesday, September 26, 2017
Hey Wendy,

I've been single for five months now and I just feel like I'm never going to be in a relationship again.

I haven't found anyone I like yet and all the guys that are interested in me haven't made a move in real life or are overly confident and are just "players.”

Talking about this makes me feel lonely. I feel like all my girlfriends have husbands or boyfriends, and I just don’t see things changing for me. Help!

AI – Seattle, WA

Dear A,

I’m sorry you’re feeling the pain of being on your own. I can relate. I promise, if a relationship is what you want, and you’re committed to having one, you’ll have one again. The two simple things you need to do to find your love are to start dating and don’t quit.