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“I Cheated on My Sugar Daddy With his Close Friend”

Sugar Daddy

I am a 24-year-old girl who started having an affair with her boss in May of 2013. It was just ok in the beginning. He was a sugar daddy, per se, and I expected a lot from him, and my expectations were not met. Or they were met too late. It put a strain on me. For example, I had asked him for my rent in January of this year — rent that was due in December — but he didn’t give me even half of it until May. Meanwhile, since I worked with him, I was quite aware of his other girlfriends. He’d bring them to the office whenever he liked, which was disrespectful to me. I knew he took these girls shopping, took them on vacations, and even bought them cars. But when I asked for something, I wouldn’t get it until six months later. I really was not satisfied.

In January of this year, a friend of my boss’s who comes to the office regularly started to ask me out. My boss and I were on and off. His friend told me he liked me, and he wooed me and all that. I asked him for the rent. I was about to lose my place. He gave me the rent. He was trying to get into my pants, sure enough. But it felt really easy with him. I didn’t see him with other women and he was very responsive. So, I began a relationship with him. It was good. Until May.

Then, he stopped calling me. And then by June, my boss stopped calling too. They are very close friends. I figured they found out about my stupid game. So by July, I couldn’t take them ignoring me anymore. The friend would come around and pass my desk like I didn’t exist. My boss would do the same thing. So I quit my job. For my happiness. But every day ever since then I have been thinking about the terrible thing I did. Especially to the friend. I have been thinking of a way to make it work with either of them.

So, which do you think I should do:

1. Apologize to them separately (and if so, what is the best way to go about it?).
2. Apologize to my ex-boss because he is the one I cheated on.
3. Just let it go and move on with my life.

— Feeling Like a Bad Woman

Here’s exactly what I think you should do:

1. Let it go and get on with your life.

2. Find a new job, if you haven’t already, that pays enough to cover your rent and/or get a roommate so you no longer have to ask random men to pay your rent for you.

3. Is your boss married? If he is, instead of thinking about how you ruined things with either of these two men, think about the woman your ex-boss is married to and how you contributed to a pattern of chronic cheating in her marriage.

4. Think about how, one day, you won’t be 24 anymore. One day you might be married. Maybe you’ll even have a kid or two or three. Imagine how you’d feel if the man you’re married to — the father of your children — was sleeping with multiple other women and spending money he could be contributing to your family and household and YOU on these “sugar babies.”

5. Stop thinking about men in terms of what they can give you or get for you. Start thinking about what you can get for yourself.

6. Stop thinking about your sexuality as a commodity (unless you really want to become a professional escort or hooker). It is so much more than that. It’s an expression of YOU — of your passions and your ideas and the way you look at the world. It’s an expression of the things you’ve learned, and the places you’ve been, and loss you’ve overcome, and the joy that has filled your heart again and again and left you breathless in its intensity. It is so much more than your June rent.

7. Do something kind for someone else. Get out of your own head and stop thinking about you, you, you, and do something that will make a difference — even a small difference — in someone else’s world. You will be amazed how a simple act of kindness has the power to change the way you think about yourself and your place in the world. You will be amazed by how thinking of someone else limits the breadth of your own problems while also empowering you to tackle them.


Follow along on Facebook, Twitter, and Instagram.

If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


Comments on this entry are closed.

Ika Ika August 27, 2014, 8:06 am

OK I could only read the 1st lines. “a sugar daddy, per se” WHY THE HECK USE PER SE???? Sorry, it´s one of my pet peeves.

Ika Ika August 27, 2014, 8:12 am

Now I´ve finished the letter and Wendy´s (awesome) advice. LW; please learn to live within your means. And no man (especially not one for whom you´re just another one of the girls he´s sleeping with) owes you a damn thing.
Take Wendy´s 4th point and further it, if you have a daghter one day, would you lke it if she slept with any guy just to make rent???

And finally, you can´t make it “work” with either of those guys. It´s quite obvious neither was intested in anything long term or serious with you.

suzyinthesky suzyinthesky August 27, 2014, 8:41 am

I KNOW!!! I had to look up the definition.
by, of, for, or in itself; intrinsically:

Ika Ika August 27, 2014, 8:48 am

Yeah. It´s somehow become the new fashionable term to butcher. At least LW spelled it right, I suppose.

Dear Wendy Dear Wendy August 27, 2014, 8:53 am

No, she just had an editor.

Ika Ika August 27, 2014, 8:56 am

I suspected that! But I thought I´d give her the benefit of the doubt in one thing haha. Silly me.

Ika Ika August 27, 2014, 8:45 am

I just can´t leave this letter alone. LW ,it´s not cheating if the guy is also sleeping with lots of women. And if you want better gifts, maybe learn some new tricks?

avatar Jenny August 27, 2014, 8:28 am

Beautiful, thoughtful advice by Wendy. This letter just made me want to bang unintelligibly on my keyboard and that is why this site is “Dear Wendy” and not “Dear Jenny”.

Also, anytime your boss wants to sleep with you it’s time to find a new job because that is just bad news. If you’re financially strapped enough that you’re almost getting evicted because you can’t pay rent, then don’t jeopardize your income source by sleeping with your boss.

Ika Ika August 27, 2014, 8:35 am

IKR? I had to bite my tongue (fingers?) soooo much while writing.

suzyinthesky suzyinthesky August 27, 2014, 8:39 am

Yeah I had to sit on my hands. Also, everything about this letter is just so, so wrong, my brain just exploded a little.

Skyblossom Skyblossom August 27, 2014, 8:46 am

No need to apologize. You used them for money and they used you for sex. You’ll get much further in life if you don’t have to sell your body to pay your bills. Consider your options for making a bigger income or for deceasing your bills or both. Have you gone to school? Can you take some classes that would lead to a higher income. Can you find a cheaper apartment or a roommate?

avatar SasLinna August 27, 2014, 8:46 am

So I’m trying to ignore the whole sugar daddy/ dating your boss business and just look at the basics of this situation. As far as I can see, this was all between consenting adults. You didn’t cheat on your boss and I’m not seeing how you wronged the other guy either. I mean, workplace affairs are a bad idea, but they participated in that too, and gave you their money voluntarily. So I’d say there’s no need for you to apologize. Be glad you’re not working there anymore and focus on getting a new job. If you ever get a sugar daddy again, do it out of the workplace. But I would advise earning your own money.

avatar Miss MJ August 27, 2014, 9:05 am

“If you ever get a sugar daddy again, do it out of the workplace.”

Yes, this. The only thing your boss should be paying you for is doing your actual job.

Aside: I hope this guy owns his own company. Can you imagine if you found out one of your employees was paying his subordinates for sex? Lawd.

avatar SasLinna August 27, 2014, 9:09 am

Wendy, I didn’t see that the boss was married in the letter, did you edit that out?

Dear Wendy Dear Wendy August 27, 2014, 9:29 am

You know what, I didn’t! Obviously, i read the letter several times and somehow had it in my head the guy was married, but you’re right — there’s no mention of a marriage or a wife. My bad. I’m going to go edit my response now. Thanks for pointing this out!

avatar SasLinna August 27, 2014, 9:37 am

Maybe it was the use of the word “affair” that pointed you toward thinking the boss was married? I’m not a native speaker and I wasn’t entirely sure about whether people would even call something an “affair” if there wasn’t some sort of cheating involved. (In German you could definitely speak of an “affair” even if there was no cheating).

Dear Wendy Dear Wendy August 27, 2014, 10:12 am

It was definitely the word “affair.” In American English, affair usually connotates something inappropriate — like extramarital intimacy — but in this circumstance, the word affair couple simply point to their boss-subordinate relationship.

Skyblossom Skyblossom August 27, 2014, 8:58 am

Your boss thought it was fine for himself to cheat on his wife, he considered it fine to have sex with his own employee and then he considered it wrong for one of his sugar babies to have sex with his friend. His boundaries are all out of whack. There are so many levels of wrong in this situation. It sounds like the only relationship he protects is his business relationship. You should run from this situation and never look back.

Raccoon eyes Raccoon eyes August 27, 2014, 9:03 am

Wendy, amazing response. I, like the dork I am, try and anticipate your advice, and usually I’m not too far off…but reading this, all that came to me is, “This is a joke, right???”
Also, how does one even request (demand?) rent money in this day and age? Am I just not enlightened enough?
Blah, whatever. LW, please live within your means, and if you truly want a relationship with a man, you need to not rely on him like a “sugar baby” or whatever.

avatar Muffy August 27, 2014, 9:20 am

This letter seems fake to me. How many friends drop by your workplace on the regular? I’m assuming the “friend” would have a job himself and may be occupied so as not to allow him to wander the halls of another workplace.

Also, ever thought of the fact that your “sugar daddies” may not have been interested in you at all but since you were ready and willing they thought they’d have a go? I mean if they’re taking other girls out they clearly must prefer them to you. Time to learn new tricks or plastic surgery maybe otherwise I don’t see how you can “get them back”.

I don’t know this letter screams fake. But if it is real you may have an std. As well as a host of other problems.

avatar jlyfsh August 27, 2014, 9:28 am

I think it probably happens more than you think. Assume maybe that this is a small to medium business and that the friend also works in the same industry. Or perhaps the friend works a job with flexible hours and visits his friend, who in this case is the boss and probably has much more flexibility in his hours.

avatar Muffy August 27, 2014, 9:34 am

I just can’t imagine someone with actual power like a lawyer, doctor, accountant, banker or successful businessman being stupid enough to bring his girlfriends in for people in the office to laugh at. But maybe I’ve never known trashy low lifes. Maybe they are like the only two people working there.

avatar jlyfsh August 27, 2014, 9:37 am

I think it actually happens more than you think and people who you would never expect are the ones doing it. Even powerful people make shitty decisions.

avatar Muffy August 27, 2014, 10:07 am

I don’t know I just get the vibe that they work at some small crappy place and his other girlfriends have acrylic nails (not gel even) and are orange and are named named Tiffani or kandi or staci or the alternative double e ending.

Ahhh this letter just infuriates me please let it be fake.

avatar lets_be_honest August 27, 2014, 11:35 am


avatar Kalu August 27, 2014, 11:36 am

My ex boss’ married friend used to drop by and flirt with me (for the record, besides being married he was not my type and too old)
He was also a business associate, so would only drop by when casually discussing a contract. Lots of people dropped by in that casual office, the kind of people who don’t have to clock in and worked nearby I guess
I have no problem believing this letter

avatar MsMisery August 27, 2014, 1:56 pm

“Friend who comes by the office regularly.”
I guess we don’t know if this means “office building” or “manager’s office.” I for some reason read it as a friend of the boss who worked in the same building but not the same department? So he’d drop into their area every so often? I guess it would be weird if it were a non-employee just popping in and out. My managers never have non-work visitors that often.

avatar jlyfsh August 27, 2014, 9:25 am

You mention that you had an affair. Are both of these people married? What would you envision your relationships with these men looking like if it ‘worked out’? Do you think they are going to leave their partners for you? What do you want from them or from a future relationship? Are you just looking for someone to fund your lifestyle of choice or do you want a life partner? And after thinking about what you want read Wendy’s advice about 10 more times.

Crochet.Ninja Crochet.Ninja August 27, 2014, 9:44 am

how about pay your own damn rent? ffs.

Amanda Amanda August 27, 2014, 10:06 am

Oh, come on now. That’s just silly talk!

bittergaymark Bittergaymark August 27, 2014, 9:52 am

I am aghast that her boss would ever even think of disrespecting her! Usually, nothing commands respect like a bargain basement — pay me when you feel like it — whore.

kare kare August 27, 2014, 9:58 am

Seriously, you always get the money upfront. That’s like Hooking 101.

Addie Pray Addie Pray August 27, 2014, 10:22 am

Also you don’t kiss on the mouth because that, but not the other stuff, is too intimate. (Things I learned from Pretty Women. Dumbest movie ever. There, I said it!)

Addie Pray Addie Pray August 27, 2014, 2:43 pm

*Pretty Woman, whoops, who cares though

Ika Ika August 27, 2014, 11:56 am

Re-reading (again) it seems she did with the 2nd guy at least: “In January of this year, a friend of my boss’s who comes to the office regularly started to ask me out. My boss and I were on and off. His friend told me he liked me, and he wooed me and all that. I asked him for the rent. I was about to lose my place. He gave me the rent. He was trying to get into my pants, sure enough.”

Kate B. Kate B. August 27, 2014, 10:36 am

A-men. You hit it right on the head.

Diablo Diablo August 27, 2014, 10:47 am

“Bargain basement” makes her sound so cheap. Surely there’s some more honorific economic term we could use, like “laissez faire.” I mean, it’s French, so it sounds sexy….. But, yes, always close the deal before you deliver the goods. The best part was how she gave it away for free and then claimed to have been disrespected. LW, kindly pull your head out of your ass and take care of yourself. Even if your plan is to be a heartless gold-digging rent-girl, you still need to take better care of yourself and make a plan that has a chance of succeeding. Use your body for what you want, that’s your business, but you are allowed to use your brain too.

Amanda Amanda August 27, 2014, 9:52 am

I can’t decide if I want to be snarky or…just slam my head into my desk. Repeatedly.
I seriously can’t wrap my head around the idea of knowing a guy wanted sex and then ASKING HIM FOR MY RENT.

avatar MissyC August 27, 2014, 10:14 am

I don’t even know how that would happen. I would feel strange even asking my parents for rent. But some dude who wants to sleep with me? Hey, let’s light some candles. Want to buy some champagne for us to pop and oh, by the way, can you also pay my rent even though we just met? K thanks.

Amanda Amanda August 27, 2014, 10:29 am

Well, at least the champagne and candles classes the whole interlude.

Amanda Amanda August 27, 2014, 10:35 am

*classes up.
Good lord.

avatar MissyC August 27, 2014, 10:45 am

It was the only way I could even think that it might even possibly come up. Then again I have not spent much time contemplating existence as a “sugar baby” (is that what you call it?) so maybe therein lies my problem. Good thing I’m almost done with work for the day…

kare kare August 27, 2014, 9:57 am

In the future when you want to make rent, sleep with your landlord instead of your boss or his friend.

(Hopefully it’s obvious that I’m being sarcastic. If not – find a better job/get a roommate/move somewhere cheaper.)

honeybeenicki honeybeenicki August 27, 2014, 10:00 am

Wait… I can just ask random dudes to pay for stuff for me? Do I have to sleep with them or can I just ask nice?

Kate B. Kate B. August 27, 2014, 10:32 am

Bat your eyes and twirl your hair. It totally works.

avatar ktfran August 27, 2014, 11:01 am

Smile too. That helps.

othy othy August 27, 2014, 12:14 pm

Especially if you’re in your early 20s.

avatar Essie August 27, 2014, 10:00 am

LW, I think you’re confusing a relationship with a business agreement. These men paid you for sex. And then they got tired of paying you for sex. You didn’t ‘cheat’, unless you had an exclusive arrangement with your boss. Which you apparently did not, since he brought other women around who seemed to have the same deal you did.

If it is a romantic relationship that you want, stop asking men for money and pay your own rent.

If you want a guy to pay your bills and buy you stuff, consider becoming an escort. Some escorts have regular customers; the arrangement wouldn’t be very different from what you had with your boss.

avatar MsMisery August 27, 2014, 1:51 pm

Exactly. We’ve all been so misled by “Pretty Woman.” BUT MY SUGAR DADDY HURT MY FEELINGS I DON’T THINK HE LOVES MEEE. No, prolly not.

bondbabe bondbabe August 27, 2014, 2:59 pm

You’re right–she didn’t cheat, it was an arrangement. However, maybe the two friends also didn’t want to be “wiener cousins.”

avatar Crazy_Pug_Lady August 27, 2014, 10:05 am

Please listen to Wendy. Firstly, Go get tested for STD’s!!! You were sleeping with men that had multiple partners, did you use protection?

like Wendy said, You need to really think about what you’ve done here, while it may have been fun and easy for you to do this while your 24 what about when your 30, 35 or even 40? Also at some point sugar daddies are going to stop knocking on your door as you get older.

Raccoon eyes Raccoon eyes August 27, 2014, 11:18 am

I love your name, Crazy_Pug_Lady! Awesome.

FireStar FireStar August 27, 2014, 10:06 am

You had a contract…Sex for money. Your contract was terminated. No need to apologize. If other girls were getting vacations and you couldn’t get your rent paid then maybe this isn’t the line of work for you. Is this truly how you want to live your life? This is what you wanted for yourself when you were a little girl? What is the end game? Just cycling through men until they tire of you? Taking whatever coin they throw your way? If you want to be a sex worker move to where it is legal and at least get paid so you know you can make your own rent. Pretending these arrangements are relationships and not business transactions fools no one but yourself.

Kate B. Kate B. August 27, 2014, 10:35 am

If the other girls were getting vacations and the LW wasn’t, obviously they were better at it than she was.

Amanda Amanda August 27, 2014, 10:44 am

Not gonna lie – I thought the exact same thing

Lyra Lyra August 27, 2014, 10:11 am

This makes my head hurt. LW, you need to learn how to fend for yourself. Pay your own rent, pay your own bills. If you can’t afford to do that, live with your parents for a bit to save up or find a roommate or two. And LIVE WITHIN YOUR MEANS. Plenty of people — just like you — who are in their 20’s make it work. They cut down on their spending if they can’t make their rent payment. They find ways to earn more money in order to make ends meet. Honestly if you don’t learn to do that now you will regret it.
Move on with your life, if you’re still at that job quit and find a different job, and I suggest staying single for a while — as in, at least 6 months. ONLY rely on yourself. Pay your rent and other bills yourself. Go out and meet new friends. Find a new hobby whether that is a new exercise or reading a new book or whatever. I think you will find being able to make it on your own very freeing and it will give you a ton of self confidence, which is something I think you are lacking right now. It is so awesome to say that you and only you are supporting yourself.

gigi gigi August 27, 2014, 10:12 am

Ugh! What EVERYBODY else already said!

Addie Pray Addie Pray August 27, 2014, 10:17 am

Do women like this, and men who go for women like this, REALLY exist? I mean, really?

avatar TheRascal August 27, 2014, 10:25 am

Wendy has far more compassion than I do.
How do people this selfish and self-centered exist? I’m baffled.

Addie Pray Addie Pray August 27, 2014, 10:38 am

I think they only exist in movies. And on DW.