Advice Column: How To Be The Other Woman When It's No Longer A Good Time

Advice Column: How To Be The Other Woman When It's No Longer A Good Time
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Sarah Diniz Outeiro

Dear Chelsea,

I am a 24-year-old woman, who has never really had a real relationship of any sort. The men I like are usually only interested in hooking up, or I am too afraid to actually tell them how I feel out of fear of rejection, or are uninterested. I would say I am fairly good looking – I actually get a lot of male attention (not that that should be a marker of my self-worth in any way), but none that is particularly tempting.

I also move around a lot. I recently moved to a small town, with a pretty close-knit expat community. I moved into a beautiful house, and my compound mates is a man I was instantly attracted to. We hooked up a few days later, and have been hooking up for the past couple of weeks. The catch: he’s 20 years older than me, and has a girlfriend. I am sort of seeing someone too, but I’m really not invested and will probably end that the first chance I get because the guy is sweet and I don’t want to lead him on.

In my head I keep wondering why this older man is stepping out of his relationship to sneak around in the dead of night with me just for a few hours. I imagined his girlfriend was dull and/or bad looking. But then he brought her to our home the other day to spend the afternoon with his parents who are visiting. She’s beautiful and 35. And must mean enough to him to introduce her to his parents. I can’t really attest to her personality, as I’ve never spoken to her – but according to my other housemate she seems nice. I have never broached the subject with him, apart from the first night we hooked up (we were both quite inebriated), and his answer was simply “I’m leaving the country in a short while.”

When he asked me “out” after that first night, he spent a lot of time flirting and had really good conversation – in fact, conversation with him is almost the only intellectual stimulation I have been getting of late and I really don’t want to lose that – but the understanding that we came to was to be discreet. I have never done anything like this before, and I can handle the emotional aspects of the equation for the most part. I know there is no future here and that we’re both just in it for a good time (well, except, of course, it would be nice to be able to just go out once in a while or watch a movie together even in just in his apartment), but increasingly the conversation and witty banter has decreased, and that was part of the appeal for me.

Plus, seeing his girlfriend in the flesh was quite jarring and I feel like it bothered me more than it should have for having known about her from the start. Also, later that evening he took her to a concert by a band we had bought a poster of together the first night we went out, after I was the one who told him about the concert in the first place (And yes, I know I need to stop being petty). I can’t help but wonder though, would things have been different if I had never known about her? Should I just go with the flow and enjoy the occasional (very good sex) on his terms? Or should I assert myself and tell him he needs to put more effort into this even if it is just a secret tryst? Or should I end it and deal with the awkwardness of having to live with my former lover? Either way, ignoring him (and hoping he’ll notice) while I listen for sounds of his car pulling into the driveway is probably not a good idea. Please advise.


Wanderlust Woman

Pablo Heimplatz

Dear Wanderlust Woman,

I’ve been so anxious to get to your letter. For two reasons, really. First, stories like yours seem to get rushed over quickly. I mean, seldom do we hear many people cheering for the other woman, right? They kinda get that side eye look, instead, that seems to say, GIRRRL, you weren’t really expecting to feel good all the time with a man who was cheating?! And so it goes, others thinking you got just what you were in for.

But I have zero patience for that kind of attitude. Because it’s missing the point. The heart of this story. Which is exactly why I’m so happy you wrote to me. Because I love picking up on what others miss. They are the pieces I care so deeply about. So, FYI, I’m not going to focus on the scandal. I’m not going to perch myself up on some moral high ground and give you a lesson about being the other woman.

Because I’ve been her too.

That’s the second reason I’ve been so anxious to get to your letter. Because you remind me of the girl I used to be. Grasping at halfhearted relationships with a full heart—without, of course, ever intending to. Trying to associate myself with a “good time” when a “good time” thrives on carelessness and when caring is the very experience that feels so good for you and I.

James Forbes

Now that I’m no longer 24, you know what my mantra is? Above all, one must care. Actually, that’s always been my mantra. But, when we’re young, I think we get twisted up with these ideas that to be fun and to have fun, we’ve got to get our heart out of it. We’ve got to turn our mind off. We’ve got to be able to be discreet about how naked we’ve really gotten with each other. We’ve got to be cool when watching the man we’re sleeping with introduce his girlfriend to his parents. We’ve got to be okay with nothing looking out of place when something has begun to feel very out of place.

Be honest, what does a good time mean for you? What does it look like and feel like? What makes it especially “good”?

Because if it was having casual sex, you have that, so you’d still be feeling good right now. You wouldn't be writing me.

My feeling is, for you, hooking up isn’t the good time, it’s simply the invitation. For you, hooking up is actually your gateway into settling in and speaking up.

You see, it’s easy to assume that we wanderlusters feel good when we’re on the move and in-between and unattached but I think that’s the illusion. I think what really makes the uprooted feel good is whoever we meet along the way that makes us feel at home.

Have you ever thought that maybe you’re in it, not for the sex and the casualty, as much as you are for that playful, fiery banter that makes you feel invested and heard, aroused and alive? Believe me, don’t underestimate the power of conversation—what we would give and even forfeit just to spend time with a person who magically makes us feel brighter.

Sarah Diniz Outeiro

As mentioned, I, too, have kept on with a man who was not only in a relationship with a perfectly, respectable woman but was engaged to a perfectly, respectable woman. And while I couldn’t articulate this at the time, the reason I was not only able to give myself to a man who was taken but was able to forfeit my own dignity and, most importantly, values in the process was because I wasn’t myself around him, that was the romance, around him I was better.

Let me explain. The good time that kept turning me on and kept me coming back was that around him I was turned on. In his presence, it was like a flip switched. I lit up. Mentally. Emotionally. Even, physically. I wasn’t lethargic. I was all light, all the time, and all perked up. That’s how I was better. I could be playful and poised. I even felt purposeful. Like, I was somewhere I was meant to be. I don't know about you, but when you’re the new girl in town, there’s something cathartic about being invited into a home—even if that home is only a bedroom. When you’ve been so busy wandering around, trying to find your bearings, even if only in your head, there’s something stabilizing about someone who looks you in the eyes when you're standing in the middle of his room. There’s even something promising about someone who is intending on using you in a certain way. Because again, when you’re just settling in and still a little bit lost, there’s nothing like having a purpose.

No wonder we wind up depending upon men we only see for a few hours in the dark of night. Because relationships of any sort make us feel purposeful. And, early on especially, they flip that switch in us that turns us on and makes us feel alive. This is why we hold on. Because we don’t want our light to shut off. And we’re afraid, not to lose the person, so much as we’re afraid to lose access to that part of ourselves. The better part of ourselves. The part of ourselves that we don't feel like comes out enough, that we assume must be reserved for the rare person. But the mistake here is thinking that the relationship itself is responsible for this element of us, when it’s not. We are responsible for this part of ourselves because that part is us. And this relationship has simply brought it to the surface. It has activated this special quality in us. It has prioritized it. And, more than anything, it has shown us what we are both capable of creating and what element in life we are yearning for more of, that we—at this time—are elevating above all else.

Sarah Diniz Outeiro

In your case, I believe that good time you are aching for is more stimulating interactions. I think you’ve fallen in love with a side of yourself that is playful and charismatic, that is mindful and intellectually alert. I certainly have a deep need for this and, I’ll tell you what, when I was moving about just as you’ve been, I ached for it even more. Because it was during those conversations, it was during that flirtation and witty banter, that I forgot how otherwise unsettled I felt, and for a brief and illuminating moment when engaged in some deep insight with a man I felt, not only at home with the better version of myself but, like I was also getting somewhere, that I was going somewhere, that I was gaining steam and generating appeal.

Or maybe it was even more simple than that, maybe the bottom line is, I felt like I was finally living my life… just as I should be. Does this resonate at all?

I want you to think about what you are really attracted to in this arrangement of yours. Is it him and what he offers or is it the person you feel like you become in his company? Intuition tells me that you are willing to be the other woman with this man, not because he is so special or the sex is even so special, but because around him you feel like some quiet part of you begins to sing.

The mistake I made up until the very tail end of my twenties was thinking that what I was so hooked on was the “good time”—on the other person’s specialness and/or our very rare connection—when the reality was, I was really just afraid of letting go of a dynamic that encouraged a side of myself that I wanted more of. I was afraid that if I ended our relationship, I would end up losing the source that connected me to a part of me that I was so rarely connected to. This is the predicament that I sense your letter is actually about. You’ll do anything to continue this good time you’re having with this man because, if you lose him and what you have, you don’t know who you’ll really talk to or how you will plug into life. You don’t know how you’ll feel better. And you’re afraid of that. You’re afraid of loneliness rushing in. That you’ll feel directionless and uprooted and anonymous.

But here’s the thing, you’re already feeling that. You’re already losing that “good time” vibe. And not because you saw his girlfriend in the flesh but because the conversation and, as you so clearly mention, the appeal has already begun decreasing. And that’s what you need. That’s actually what you’re hooking up with him for.

Sarah Diniz Outeiro

This is good news. You know why you were with him! And it’s a reason that really has very little to do with this man himself. Trust me, you are the conversation and you can bring that into healthier relationship dynamics, and that healthiness, that honesty, is what’s going to make a relationship feel real for you. It’s going to be why it feels good.

When I was your age, I just didn’t want to see it this way either. Instead, I wanted to romanticize my issues. I wanted my struggle to be romantic in nature because it was too daunting to acknowledge what I was actually struggling with, which was the reality that I rarely felt connected to myself. And because I was always moving, the closest place I had gotten to belonging was inside of a relationship, which is exactly why I tried to make a home out of unavailable men. Because I no longer knew how to be available to my life and to myself, let alone to love.

So, to the girl I used to be, it’s your turn to figure it out.

Because you can.

Start by letting this man go. Drama free. You can let it fizzle out naturally. Or you can be clear and caring and, yes, casual about it. Tell him you’ve enjoyed him, especially figuring you were new in the house, but the more honest thing to do is to attend to the lives you have that you don't have to be so quiet about. Say, it’ll feel good this way. It’ll feel better for you. He’ll be gone soon anyway and, the reality is, he never was really there though there is romance in thinking so.

Now your focus needs to be on you, on coming home to you.

With this move, let the next chapter of your life be about about no longer keeping yourself from what a good time really means for you. Let it be about no longer rejecting yourself.

In this next chapter, care openly. And continue to find those people who make your mind buzz and your heart sing with words. Make friends with them. And when you have no one to talk to deeply, explore life deeply on your own. Write. Write letters that you never need to send. Or, like we’re doing, write to people you don’t even know. You may be surprised how much they feel like they already know you and how they’ve been rooting for you all along.

Because, remember this, we’ve all got a bit of each other in ourselves.

That’s what any real relationship is about, by the way. It’s about finding those bits and seeing them really.

I think you’ve done that. I think you’ve had more real relationships than you realize.

You’ll have better and you’ll have more. And with them, you’ll have more good times where you don’t have to act casual or careless.



Sarah Diniz Outeiro

PS: Don’t forget to give love—affection and time—on your terms. To do otherwise, is to reject yourself before a man is even able. Don’t self-sabotage yourself, my friend. You are more wise than that.

PPS: All the years I spent clinging to my lovers were the years I was longing most for a friend.

PPPS: Final question, in the moments when you and this man were talking, did he feel like a friend? If yes, then you don’t need another hookup right now, you need a friend. That’s the realest relationship you need.

Toa Heftiba

A Breakup Coach trained and certified in Solution-Focused Life Coaching, Chelsea Leigh Trescott helps her clients connect the dots and find the meaning in what’s been lost. Seeking advice? Send situation and question to for a chance to be featured. For coaching services, including e-coaching services, please visit

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