I’ve Been Married 20 Years. Now, My Wife Wants A Threesome With Her Best Friend

by Rebecca Endicott
Becca is a writer and aspirational dog owner living in NYC.

Got a question about life, love, or any topic in between? My weekly Ask Becca advice column is here to help!

After all, nobody’s life is a straight path; we all face complicated challenges every day. With that in mind, the team here at LittleThings wants to help out in any way that we can!

If you have a puzzling question or difficult dilemma and you’d like some advice, you can always send it to!

Every week, I sort through our reader responses to track down important questions that touch on problems that we can all relate to.

Last week, I talked about crushing on a neighbor, sexual health stress, a friendship with benefits, and how to know if you’re moving too fast in a new romance.

This week, I’ll tackle new topics, touching on a dad who keeps racking up DUIs, a teenage child grappling with identity issues, a dynamic duo of unkind exes, and whether a threesome is ever a good idea.

Scroll through below for my very best advice. And don’t forget, if you have a question, send it my way to!

And if you have advice of your own, make sure to let us know in the comments!

Dad's DUIs

Mother finds out her daughter is being driven by dad with DUI
Laura Caseley for LittleThings

Hey Becca,

I left my daughter’s dad when I was pregnant. He was a drunk and not a very nice one at that. He is a multiple offender of DUI’s and currently does not have a license.

I let him be there when she was born, and up until she was about 6 months old, he got to take her every other weekend. There was one condition, that he not drive a car when he had her.

Well, of course, he did! So I stopped letting him take her.

He recently got another DUI, along with other charges. I want what’s best for my daughter and would never want her in harm’s way, nor in the environment that her dad lives in.

Still, I feel like a horrible mom because I don’t want him ever in her life again!

I’m scared to file papers for custody or child support because I’m afraid I’ll be forced to let him see her, but no judge or anyone else can make me put my daughter in harm’s way. I keep arguing with myself back and forth to bring him back in, but I always choose not to.

Choosing to be a single mother was never in my plans but I have made it without him. What are your thoughts on what I should do?


Becca's Best Advice

Dear Anon,

You did an incredibly brave thing for the sake of your daughter. It takes a lot of courage to end an unhealthy relationship and voluntarily take on the challenges of single motherhood.

From what you’ve said, it seems pretty clear that your ex seriously needs to clean up his act before he can be a part of your daughter’s life. It’s unacceptable for him to expose her to the risks that his history of drunk driving pose.

Still, I wouldn’t count him out entirely at this point. People who struggle with addiction, like your ex, often make choices under the influence that are completely at odds with who they really are. If he is able to get clean, he might be a much better father in the future than he is right now.

Your daughter will grow up someday, and she might want a relationship with him. He may even be in a place to be a good father to her.

I know you say you “never want him to be in her life again,” but that could change if he’s really willing to change and be a responsible parent.

As to the issue of custody, I’m not a lawyer and can’t comment with any kind of expertise. However, my feeling is that it’s always better to take control of the situation from the outset and consult with a legal expert as soon as possible. Only a lawyer can advise you about establishing a plan for legal and physical custody, visitation, and child support.

Remember, you are a brave mama, and you’ve done a great job so far! You will be able to handle any challenge that comes along.


Child In Transition

Mother is confused when daughter wearing makeup a few months ago now insists she is a boy
Laura Caseley for LittleThings

I have a 16-year-old daughter who suddenly has announced that she is a boy, and that she has always been one.

I think she is just confused about her place in life. I have looked and thought back through the years to see if maybe she showed signs that she may have wanted to be a boy, but there hasn’t been one sign at all.  And this isn’t just ’cause I’m in denial.

I feel I’m an open-minded person and I could accept it, if that is what she truly wanted. But up until a couple of months ago, she had never acted this way. She has done a true 180 in her ways.

I just don’t understand how you can change your entire way of thinking in literally months. I mean, seriously, she was just wearing makeup and painting her fingernails about four months ago.

She has never leaned towards anything that we consider boyish. And trust me, I am a complete tomboy myself.  So, I’m worried about what I should do.

It doesn’t seem normal to me that this complete change of mind happened so quickly. She does have a couple of transgender friends in school. This makes me think that she is just trying to be accepted by them, so she is being like them. She has in the past changed her mannerisms and speaking ways to run with the group.

Can you guide me in what I should do or how I should handle this?


Becca's Best Advice

Dear Anon,

In your letter, you talk about your daughter and use the words “she” and “her.” For the purposes of this response, I’m going to refer to your child as your son, and use the pronouns “he” and “him.” I hope you will understand that this is not a judgment of your words, but an attempt to acknowledge what your child is telling you right now.

Transgender identity is an incredibly complex topic, and many people (even most people) have no idea how to discuss it. That’s especially true of parents who may think that they raised a daughter, only to discover that their child views his or her own identity entirely differently.

My advice? Take your son at his word, and accept that he sees himself as a boy. And don’t forget to tell him, “I love you, and I’ll always be here for you no matter what.”

In your letter, you write, “I feel I’m an open-minded person.” I think this is probably true. You clearly love your child very much, and want what’s best for him. It’s a tremendous gift that your son trusts you and loves you enough to share this part of himself with you.

Your main concern is that his desire to live as a boy is a “phase” or an attempt to fit in with his trans friends. Is that possible? Sure. Is it likely? No, not even a little bit.

We’re living in a day and age where people are largely more tolerant than ever before in history. Still, transgender identity is incredibly stigmatized. It’s also important to note that living openly as a trans person is still very, very dangerous. Very few people would choose to go through the challenges and dangers of transition lightly.

Your son has done something very brave by confiding in you. As his mother, all you need to do in return is offer a stable and loving safety net as he grows up and puts together the pieces of his own identity along the way.

There’s no doubt in my mind that you are an awesome and loving mother, and no one knows that better than your kid!

Love and warm wishes to you both,


Unkind Exes

Fiance does not defend himself who he is talked down on by two exes
Laura Caseley for LittleThings

My fiancé and I have been together for going on three years and we are very happy together.

He has four beautiful children from two previous relationships and we have one together; I couldn’t love those children more.

The problem is with the two exes.

The issue isn’t with how they treat me — I’m a big girl and I can take it — it’s the way they treat my fiancé and what they tell the children.

I have told him time and time again that he needs to stand up for himself, but he wants to avoid confrontation because they are the type of women who will use the children as weapons to hurt him; they will keep the kids from him for months at a time.

He got slightly behind on support payments (he’d lost his job), but he is busting his butt to catch back up. Yet they still treat him like garbage.

I am doing my best to support his choice to not confront but I am so annoyed and frustrated by how they treat him; he is a good man doing the best he can. I just don’t know what to do.

Heartbroken Love

Becca's Best Advice

Dear Heartbroken,

Your fiancé is a lucky man to have such a loyal lady in his life! You want what’s best for him, and you’re trying your hardest to look out for his interests.

That said, I’m not entirely sure that a “confrontation” with his exes would solve anything here.

Confrontation of any kind tends to make people dig in their heels and fight even harder for their position.

In the case of these two women, that might have unpleasant results for everyone, especially the kids.

Instead, I would suggest mediation or some kind of family counseling.

I agree that your guy needs to have an honest conversation with both of these women. It’s not healthy for them to poison the kids against their dad, and it’s not healthy to use time with the kids as a bartering chip to get something out of him.

Still, by the same token, they are totally justified in wanting to receive child support in a timely manner.

Here’s how counseling would help solve these problems: A mediator or counselor could help your fiancé come up with a payment plan for child support that takes into account his period of unemployment. A professional could also help them hash out some of the bitter disputes between them and get everyone on the same page, for the sake of the kids.

After all, the kids are the real victims here, more than any of the adults. They need to know that the grownups in their lives are fighting for them, not over them.

If your fiancé develops better relationships with his exes, it will be a huge step in the right direction for everyone.

And if you join in? All five kids will know they have four loving parents with their best interests at heart. That’s a pretty good deal.

Wishing all of you a happy and unified future!


Is Three A Crowd?

Wife is concerned with the possible outcome of a threesome with her husband and best friend
Laura Caseley for LittleThings

Hey Becca!

My wife and I have been married for 20 plus years. Our sex has diminished lately and we’re having it less and less each and every passing day!

I think we need to spice it up a little bit!

She has hinted at perhaps having a threesome with one of her friends, who has openly admitted to my wife that she finds me attractive. This sounds amazing!!

Yet, my wife is afraid that I might fall in love with her friend! I welcome the opportunity — however, do you think it will enhance our sex life without damaging our marriage?

I reassured my wife that as long as she participates, all will be well!

Your advice please!

Energizer Bunny ‎

Becca's Best Advice

Dear Energizer Bunny,

Wow! You certainly have found yourself in quite the position.

There are plenty of folks out there who might feel envious, and many others who would instruct you to run, fast, in the opposite direction.

I’m going to take the middle ground. In my opinion, a positive attitude towards sex makes for a happier life. Whatever innovation consenting adults dream up in the bedroom, I’m all for it.

That said, introducing a third partner to a committed relationship is very tricky ground.

You and your wife have been married for 20 years. In all that time, have you ever tried any other strategies to spice things up?

If you want to add a little zip to your sexual relationship, I would start small. Think silk blindfolds and massage oil, rather than polyamory.

I would also note that your wife sounds less than enthusiastic about the whole situation. Her friend is interested, and you are interested, but is she actually on board?

If she isn’t actually game to try a threesome, this won’t be fun for anyone.

Alternatively, it will be temporarily fun for you and the friend, followed by awkwardness and tension between all three of you. I somehow doubt that a threesome would make you fall for the friend, but it could have a profound impact on how your wife sees you.

Before you jump into anything, talk to your wife. Make sure she’s truly interested in exploring a ménage à trois.

I would also suggest introducing the fantasy in the bedroom before sampling the reality. Once you’re sure that the two of you are genuinely on the same page, you can gauge her friend’s interest.

If she seems like she’s trying to snag one of you for herself, steer clear.

If it seems like she’s just a happy-go-lucky bon vivant who just wants to try something new, go for it! Just make sure you know that everyone involved is on board for the journey.

Best of luck, and happy adventuring!


LittleThings writer Becca
Laura Caseley for LittleThings

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