Continued Continued

The TFD Book is Here, Hooray! Order It Now!

Click here! Click here to get your copy!
Image of TFD Book

Breaking Up With A Rich Guy & Standing Up For Yourself At Work

Ask Chelsea Anything_Graphic_title card_v2

In this week of Ask Chelsea Anything, I’ll be tackling two questions which are about totally different spheres of life, but which come back to the same final notion: defining your own worth. Whether it’s at work or in our relationships, we all have to do it, and it starts by being honest about what’s really going on. So let’s get to it, and don’t forget, if you have a question for me, send it to

I might have a good answer for you, and if nothing else, my robust career in being a hot mess might just provide a cautionary tale!

Hi Chelsea

Today marks my fourth anniversary with a man I love, but whom I do not want to marry. I know that we are going to break up, and I know that he senses it, too (90% of our interactions at home the past few months have been arguments and silence), so I don’t feel guilty or conflicted in my choice. I’m going to be the one to end it, because he’s not the type to actually, formally end things, but it’ll be a pretty smooth breakup, except for one thing: he is rich, and I am (relatively) poor. We live in NYC, and he makes nearly $200k a year, and I make $33k. We live in a big one-bedroom in the East Village where I have a little home office nook and can have as many friends over as I want without crowding the place or bothering roommates. Essentially, it’s the New York City dream, and when I look at the kind of rooms I can get for my soon-to-be $700/month budget, I cringe. My lifestyle is about to take a huge hit, and I admit that it is the major reason I didn’t break up with him six months ago, when it was first clear that we were not headed towards happily ever after.

So, my question is, how can I buffer this transition, and how can I get over my fear of losing out on this lifestyle of travel, nice things, and a big East Village apartment?


A Superficial Bitch, I know

Okay, so there’s a lot to unpack here, but I guess the first thing I should say is that you’ve put a pretty bow on it, but you’ve been spending at least a half a year with a man you do not want to be with because of his money. Now, I’m assuming you would not consider yourself a sex worker (nor would society, probably), but this is a grey area that so many women (and some men, I’m sure) find themselves in, where they justify a behavior that, when analyzed on face value, is pretty morally fucked.

In fact, I’d say it’s amoral in a way that sex work is not, because — at least when consensual on all sides — the person paying for the sex/closeness/attention at least knows what the deal is. For all you know, your boyfriend still thinks he’s in a relatively good relationship with a woman who loves him and intends to move forward with him, but she’s just been sticking around for months on end because of the perks. This is fucked up, and an exchange of romantic attention for money which I’m sure you wouldn’t be comfortable with under most other circumstances, but you have to be brutally honest with yourself about what you’re doing. You are with a guy because of a lifestyle he can provide to you, and exchanging time, attention, and sex for the privilege of having that lifestyle.

Now, do I think this is inherently fucked up? Eh, no, I’m very pro-sex worker/sugar baby/however you make your money. And I know that in the very real market of human life, romantic attention is a powerful commodity that should be compensated if all parties agree. But the bare minimum is that both parties need to know what is what, and your dude, I’m guessing, does not. You’re using him, and disrespecting both of you in the process.

Your life is going to take a hit, yes. But no hit could be harder than the realization that you’re essentially tricking a dude you used to love into funding your glamorous NYC life. And no one can put a price on the self-worth and pride you gain from deciding, hey, I am capable of and willing to support myself, and I’m going to do it on my own, no matter the difficulty. Because you can have all the things you currently have, eventually, you just have to work for them. And I can promise you that those luxuries will be all the sweeter when someone can’t take them away from you, or when you don’t have to carry on a fake relationship to keep them.

In the meantime, get a cheap room in a neighborhood that isn’t the East Village and sign up for Mint or YNAB or some other basic app to help you get in control of your money. Pick up a side job or start really concentrating on your current job to start making some serious moves — enjoy feeling the professional fire under your ass that was dulled for years by someone else’s success. We’ve all had to do it, and from experience, your crappy little room or studio or whatever starts to seem really exciting and kind of luxurious when you realize it is really, truly yours.


Before I get into the question, I’ll give you a little background. Right now I am getting my Master’s degree for Library and Information Science. To pay the bills, I work at a premier retirement community as a receptionist, although my fancy title is Resident Service Specialist. The job is not at all as glorified as it sounds, and is in fact, pretty unorganized. There have been 2 instances where I have been working and things have gone missing. Now, neither of these instances were because of me or caused by me in any way, but because I am working at the front desk, it seems I get blamed and therefore, I can’t help but feel blamed even though I do not think I should feel that way. But essentially it’s a classic case of I’m at the wrong place at the wrong time kind of thing. I feel that this feeling I have is caused by people who are more important than me deciding it is easier to blame me than to handle the problem in a better way.

I am wondering if you have any advice as a woman running her own business, how people who are working as receptionists, or positions similar, can feel empowered and, I guess, guilt free. I don’t like feeling like I should feel guilty just because I happen to be the easiest blame.


Well, Anonymous, I’m not going to lie — your situation sucks. It sucks to be at the bottom of any totem pole, but it especially sucks at work, where you can find yourself taking the blame for any number of things which were not your fault, but which your managers seem content to push on you. (For what it’s worth, in any decent corporate structure — and this is what can sometimes make the service industry feel so crappy — a good manager takes the responsibility for things that aren’t even her fault.) All that said, another reason they could be giving you this specific pile-on is because you are currently a grad student, and therefore not in this for the long haul, which can lead to a (totally unfair) assumption that you aren’t as serious about your job. For more insight, I spoke to my HR friend Dani* again, to get her take on the issue. She said:

The truth is that people just don’t really value you as much as an employee when you’re in a low-impact position and going to school, because they know the chances you’re going to stay at this job and move upwards are pretty low. It’s not like you’re in a corporate managerial position and going for your MBA, which will then be put back into your current career. You’re doing something that’s likely going to take you out of whatever you’re doing.

This means that there’s probably more than a little feeling of “Oh, who cares, it’s not like she’ll be here that long anyway.” This can often mean you’ll be pushed around, tasked with shitty jobs, or, as in this case, blamed for things. You have to let them know, in a way that won’t get you fired, that you’re not here to be their temp. You actually work there. If I were you, I would send a thoughtful email to everyone higher than you who has been blaming you for stuff, simply and concisely asking what you can do in the future to monitor prevent things like this, without accepting blame for it. Let them know you are invested, too, and speak to them as an equal. Not a subordinate.

And on a more philosophical level, Anon, I’d say that when it comes to “feeling blamed” or guilty in some way, simply, don’t. Do what you can to assert yourself within the confines of your job, and don’t think of it as beneath you (even if it’s a falsely-inflated receptionist gig, which I understand can be frustrating). But ultimately remember that if you are not being treated with the respect you deserve, that is not your fault, and it’s not something you should feel guilty over.

If nothing else, allow this time in a low-respect position to teach you how not to be a manager or leader, for when you become one later in your career. Remember what you are good at, and all of the things that define you beyond this job, and that being treated in a less-than-generous way at this job is ultimately a small problem on the scale of life. You have to decide your value, and even as an entrepreneur, I’m faced every day with clients or peers who do not treat me as a businesswoman, or even with respect. I have to remember that my value and meaning exists beyond them, and that all I can do in that individual situation is be honest and have confidence in myself. That’s all you can do, too. It’s all any of us can do.

TFD Social Banners_Twitter-01

  • Jean Livingston

    In regards to the first letter, the beginning of Chelsea’s response was pretty judgmental. The author of the first letter is trying to ask for advice in order to overcome her faults. I understand that Chelsea is trying to be honest about the situation, but the girl already called herself a “Superficial Bitch” and we only have a single paragraph to base their relationship off of. All we know is she is aware she wasn’t doing the right thing by staying with him and she’s asking for help in overcoming her fear so she can make the right decision.

  • Rebecca Spence

    The first response is a little harsh, don’t you think? At least the girl recognizes she needs to move on but, hey, ending a long-term relationship and the idea of a dramatic lifestyle change might take a few months to get used to. That said, it’s certainly about time she started looking for a new place to live (and a roommate or two).

  • Woah.

    That first response was way over the top.
    First it started out as what appeared as thinly veiled slut-shaming.
    If this woman loved this man and had it wane, or is watching a relationship die and realized now that her life finances are changing, that response would immediately isolate her.
    That really didn’t stick up for the team this time.

    A Superficial Bitch, I Know,
    You’re in a pretty pickle. But I hope you know that many people have been there before you, financially and romantically. There will be changes, heartbreak (maybe), but ultimately, growth. I hope you bring this up in a calm way, have a conversation with your partner and discuss how you see this, necessary steps forward and if you can have some time to get ready. Start building your foundation now and be willing to step out on it when you see fit.

    • chelseafagan

      Hey, I would never slut-shame her, nor is my issue with anything to do with sex. Quite the opposite — I am fully supportive of women doing whatever they want with their bodies, with confidence and dignity. But that hinges on a core thing: honesty. We have to be honest with one another about what the deal is, and spending six months dragging on a relationship that you are checked out of because it affords you a level of income is a very conscious choice, and is transactional, whether we like it or not. He’s just not informed of what’s going on. (And let’s be clear: she’s not risking homelessness if she breaks free. As she freely admits, she risks renting a room in Queens or something.)

      If she were to say to him, “I feel that we are [insert preamble to some kind of breakup here], I need some time finding my own place, etc etc,” that would be a lot more compassionate than just keeping the appearances of a relationship for as long as the benefits keep rolling in.

      I feel strongly about this because our society has such a strong, awful vitriol against women who trade some kind of romantic or physical attention for material compensation, but yet see relationships like this every day — where there is some kind of falsehood being acted out in the interest of financial security — and see that as totally acceptable, and totally separate.

      Someone’s ability to tell themselves that what they’re doing isn’t wrong hinges on this really false and dangerous dichotomy. Transactions are fine, just be honest about them.

      • Jean Livingston

        I’m not sure that this situation is “a falsehood being acted out in the interest of financial security” because I’m guessing that she didn’t go into the relationship with that intent and she’s planning on moving out because she realizes its wrong to continue to mooch off of her boyfriend’s money. No one is saying that what she did was acceptable, just that your response was harsh based off the circumstances.

      • I understand that. That could be an entire article. Relationships grow, change, and need constant reevaluation.

        However, in an advice piece, I feel labeling the inquirer before trying to help out there situation is unnecessary. Someone who felt comfortable enough to ask this question shouldn’t be immediately labeled. If this honesty discussion came later in the paragraph, or perhaps as based on “being honest with yourself and your partner” instead of viewed through the lens of sex work, which has so many connotations, and she didn’t mention. That could be okay.

        I want to help this person get to where she wants to go, since she seems to be in a quagmire right now. I didn’t quite see that in the answer this time. But I’ll keep reading, because I know you produce quality content, consistently.

        • chelseafagan

          Thank you re: content.

          But it is precisely *because* of these connotations that I bring up the issue, because a lot of what allows these situations to happen is because we see certain transactions as being more “okay” than others, or “not like those women.” And it’s one thing if you aren’t sure if you want to break up, but if for at least six months you’ve wanted out and choose not to, you have made a conscious choice to trade something for something else — a relationship (however false) for continued material comfort.

          Do I think she is a prostitute? No. Do I think women, because of many gender norms, often have a hard time being honest about the transactional nature of certain relationships? Yes. And I think that is really worth considering, particularly given the very connotations you mentioned.

          • I might find your response to be appropriate and non-judgemental if it actually responded to her question. but it seems like you were so eager to coopt her personal problem into a conversation about female morals that it blinded you to the fact that she still loves the guy (as she said in her first sentence). It’s really hard to break it off when you love the person but don’t see it working out and your lifestyles are so enmeshed. You completely overlooked when you harshly said ” you’re essentially tricking a dude you used to love…” I appreciate you have a point of view re: staying in a relationship solely for money. But that’s been addressed in opinion pieces on TFD before and this advice column is not the place to do it, just like this poor woman is clearly not the gold-digger you’re portraying.

          • chelseafagan

            I don’t know who this woman is, I have no vested interest in judging her. She said, very clearly, that she has known she no longer wants in this relationship for six months, but stayed in it because she wanted the elevated lifestyle (and “cringed” at the rooms many, many New Yorkers actually live in). If we don’t see eye-to-eye on that part of her story, we’ll probably never agree, which is fine — but I did answer her question. Mint, some hard work, and getting real about what she’s actually doing will be her saviors.

          • She is obviously staying in it because of financial comfort, but I think you’re assuming alot that very clearly isn’t there–because it fits into this transactional point you’re trying to make. If we take her language at face value, she loves him and he knows it’s over but doesn’t have the guts to end it. But you’re blaming her for “falsehood” and “tricking.” You have no idea if she is even having sex with him or giving him romantic attention in exchange for this financial security. You have no idea what transaction is going on here or if he is using her. Maybe he’s staying in it because she does more housework or its nice to have her as arm candy. Like you said, you don’t know who this woman is and the nature of her relationship. She asked for advice on getting out, you gave her three paragraphs of moral judgment. Like I said, it’s fine to talk about transactions but this may not be a good example or a productive place to do it.

          • chelseafagan

            Agree to disagree. It happens!

  • disqus_Ke3yRpgNZX

    The first response was inappropriately harsh. Yes, it is a not-good thing to realize you no longer love someone and stay longer than you should because the logistics are a lot to handle. It’s also something that happens to a lot of women, and they deserve empathy and compassion in handling this transition, rather than being called prostitutes.

    • I think it’s valid and fair to point out that it’s unkind to effectively string someone along when you no longer love them because of their salary, but on the other hand, $220K to $33K is a HUGE margin and I don’t really blame her for recognizing that sticking around will keep her lifestyle stable for a little longer. No, she’s not being abused, but that doesn’t mean that there aren’t things she needs that she won’t have access to without his money. Chelsea has been very transparent about all the help she’s gotten building this business, and it’s possible this girl’s in the same situation. It reminds me of that Salon essay from a while back where a writer admitted that she was only able to pursue that career because her husband was loaded and could support her.

      I think in reality, this girl recognizes that she needs to leave and is just trying to figure out how to do so without having to take too steep a hit to her pocket, which I think is brave and mature. Women stay in shitty relationships for money all the time. If we lived in a more equitable society maybe it wouldn’t be so common.

  • Sindhoo

    I think although surprising (not necessarily in a bad way), Chelsea’s answer/tone on #1 was spot on. The person’s question was “how can I buffer this transition, and how can I get over my fear of losing out on this lifestyle of travel, nice things, and a big East Village apartment?” meaning she freely admitted to being afraid of losing an upscale lifestyle.

    This isn’t a scared, financially abused woman who doesn’t have anywhere to go and doesn’t know what to do; this is someone who needs help starting this transition even though she knows it needs to happen. That scenario calls for exactly the tough love tone of Chelsea’s answer.

    • jdub

      Yes! I loved her answer. She didn’t mince words. Sometimes the catalyst for change is strong discomfort or shame. If this woman takes Chelsea’s advice to heart and actually takes that terrifying first step on her own, then it’s worth coming off as a little cold. I’ve been the person to stay in a fully unhappy and unsatisfying relationship for way, way too long, just because of the comfort and stability it provided. I didn’t even realize how worth it the trade-off was until like… 6 months post-breakup, when I finally felt strong enough to stand on my own two feet.

    • Hailey

      Agreed! As someone who was previously in a very similar relationship, it was absolutely “transactional.” Not that there’s anything wrong with relationships of that nature–but it’s only okay if both parties are aware and willing participants. I wasn’t being honest and stayed only because I was comfortable, and I didn’t realize until later how absolutely awful that was! For both of us! It would have saved both of us a lot of heartbreak and discomfort if someone had called me out, and I would have been able to realize sooner how great it is to build your own life. Honesty is harsh sometimes, and she was asking for an honest opinion.

  • Scissors

    I mean, isn’t the real answer that she needs to break up with him and find another sugar daddy? (is it that TFD readers tend to be in low-income girl/high-income boy relationships or is this just the norm?)

    I think the sad part is realizing how much of his time she’s wasting. He probably has a stressful job, he comes home to silence and fighting and she’s staying so she can throw dinner parties. And this has been going on AT LEAST six months.

  • Christina H

    I started having the same problem with my boyfriend and as I was corrected with depression. I did go to see a doctor and he told me pretty much the same: it’s all in my head, performance anxiety, stress and so on. I agonized for a long time but my friend recommend me one website for a dating. I meet a boy. Now I am happy. On ex-boyfriend I don’t care. Girls, check it