It’s time again for Shortcuts. For every question, I’ll give my advice in three sentences or less, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go. Today we discuss sugar babies, crushing on the bossman, and getting “closure.”
I am in a committed relationship with my boyfriend but at the same time I’m thinking about having a sugar daddy to help me out financially. Obviously, if I have a sugar daddy, it would have to be completely discreet, but at the same time isn’t that cheating? If I did have a sugar daddy, should I tell my boyfriend? Or what’s done behind one closed door shouldn’t be surfaced through to another? Am I crazy to seek out a sugar daddy that could help me out? – Confused Sugar Baby
Yes, prostituting yourself out while in a serious relationship with a guy who is unaware of your extracurricular activities is, indeed, cheating. How about maybe getting a job waiting tables?
I work in a large office and the problem is I really, really like my boss. We are both single and around the same age (early 30s). He’s cute and smart and interesting… just overall great. He’s always joking with me, and I know he is looking for a girlfriend. If he were a normal coworker, I would ask him out in a minute. However, as my boss, he reviews me and determines my ratings. I am pretty sure there is no way we can date while he’s my boss, and I feel like even if I switched teams, it would look weird to start dating someone who had managed me. Is there any way this could work out? Or should I just give this up? I know there are a lot of other men out there, but honestly I haven’t met many as great as he is. — Crushing on the Boss
If you’re able to switch teams relatively easily, I’d do that as soon as you can. That way, you can make sure the feelings you have for your boss are genuine and not just enhanced by the idea that he’s forbidden fruit. If it turns out your feelings are genuine and they’re reciprocated, I’d think the elation you’d feel to finally pursue the person you want would trump any feelings of “weirdness” that you might have getting dinner with a guy who once rated your job performance.
I have been dwelling on an old relationship that ended over two years ago. After my ex-boyfriend and I broke up, I had a lot of trouble getting over him. The terms of our breakup were never really made clear and it really bothered me. He had a lot of personal problems that he didn’t want to deal with at the time, and that I naively ignored. I never really knew whether the breakup was because of me or — and this is what I assumed was the case — whether it was because of his problems. He wanted to remain friends but this didn’t happen because I wasn’t OK with just being friends. Now time has passed but I still miss him. He was a very large part of my life (my first real love) and we haven’t been in contact since early 2011. Am I crazy for wanting to see how he is? Is this me still clinging to false hopes or is it just me caring about someone who was very important to me at one point in my life? — False Hope?
I suspect you already know the answer to your last question. If I were you, I’d try to accept that someone who hadn’t reached out in almost a year and a half probably has no interest in rekindling anything, and you’re better off honoring the special time you shared by keeping it in the past and moving on.
*If you have a relationship/dating question I can help answer, send me your letters at firstname.lastname@example.org and be sure to follow me on Twitter.
Muffy April 27, 2012, 9:04 am
hahahaha to number 1!! No LW, as long as the other man pays you to have sex with him then it’s not cheating!
John Rohan April 27, 2012, 11:24 am
I have a hard time believing the letter was sincere.
Muffy April 27, 2012, 3:17 pm
yeah no kidding! Or else the world is a very sad place
AKchic_ April 28, 2012, 12:37 am
The world is a sad place. There are individuals who have and who do actually attempt to work this scenario.
Raj May 18, 2019, 8:27 pm
There are actually alot of sugar daddies that just want someone to talk to someone or take them out to dinner, not all of them are in it for sex. I have a SD and a boyfriend. My boyfriend is aware of my SD and my SD is aware of my boyfriend and they are both fine with it. My SD lives across the country so he send me money and gifts just to talk to him and be a companion to him. Am i a prostitute for chatting with him? You all can judge all you want but I probably get more talking to this guy than I would making myself miserable with a 2nd shitty job.
PFG-SCR April 27, 2012, 1:39 pm
“No LW, as long as the other man pays you to have sex with him then it’s not cheating!”
Exactly! Then it’s a business transaction, and she ought to be prepared to Schedule C that income at tax time!
katie April 27, 2012, 9:12 am
yay shortcuts!! i love these… haha
Nadine April 27, 2012, 9:16 am
Get a job? Nah, cheat on my boyfriend. Much better idea.
Anna April 27, 2012, 9:20 am
Wow…not sure if it’s just me but the whole idea of sugar daddies and sugar babies creeps me out. I don’t have much, but I worked hard for everything I have and that makes me feel good. You should probably just find a way to make money legitimately instead of cheating on your boyfriend with pervy old men who happen to have money. *shudder* If someone said this to me 10 years ago, I would have handed them the “help wanted” section of the newspaper. Since it’s 2012, here’s a link to my favorite job search site. It compiles search results for many different job search sites.
theattack April 27, 2012, 11:56 am
The “help wanted” section of my newspaper is full of ads like “I’m a beautiful green eyed blonde looking for a mutually beneficial relationship with a mature man…”
MsMisery April 27, 2012, 1:37 pm
The “help wanted’ section of my newspaper is full of ads like “Stuff envelopes while working at home! $1000 a week!!!!” And other things I can’t possibly take seriously. I am pretty sure a Nigerian Prince is behind all of them.
lets_be_honest April 27, 2012, 1:43 pm
That Nigerian prince is sending me a TON of money as soon as he processes the paperwork I sent him along with a small personal check for only $5,000. Its almost too good to be true!
comatus April 29, 2012, 5:15 pm
Furthermore, that pervy old man doesn’t just “happen” to have money. He most likely worked hard for everything he has, too. Which would make him the honest one in this proposed relationship — the only honest one, if you don’t count the boyfriend, and it looks like you don’t.
We’re not discussing what kind of woman you are; you’ve settled that. You’re quibbling over price. Tell you what: stand in front of a mirror, look yourself in the eye, and keep saying, “I’m a whore.” When you get comfortable with that, try it with your boyfriend in the room. Once he’s cool with it, you’re going to be a very wealthy woman. Good luck with that.
bloodymediocrity May 19, 2019, 10:05 am
LW1 – You can be a sugar baby and have it not be cheating, as long as you have a boyfriend who knows what you are doing and is ok with it. Does this seem like something your current boyfriend would be ok with if you talked to him about it? If not, then either nix the sugar baby idea or find a different partner.
Addie Pray April 27, 2012, 9:21 am
LW1 – Remember Sugar Babies the candy? I miss those. Do they still make them? That’s all I have to say about your letter.
LW2 – There probably is a policy against supervisor/subordinate relationships but, even if there’s not, it’s a really bad idea for so many reasons. I say switch teams and let love conquer all! (I’ve been watching silly movies again, they’re messing with my head.) But are you sure he feels the same about you? I don’t see why you can’t just do what every respectable person would do in your position: get him drunk outside of work and see what happens!
LW3 – Remember when Rachel needed closure on Friends? Just don’t do that!
jlyfsh April 27, 2012, 9:29 am
AP they do indeed make those candies. But, they stick in my teeth and I can never eat more than 3 before getting annoyed.
Haha and I love your friends reference!
Addie Pray April 27, 2012, 9:30 am
But that’s why they’re so great – they get stuck in your teeth and stay there forever. and you can taste it for hours later. it’s the gift that keeps on giving!
ktfran April 27, 2012, 9:48 am
And your responses, Addie Pray, are the reason I’m excited for the next Chicago DW meetup!
Do you like how I plugged our outing?
Addie Pray April 27, 2012, 9:55 am
Oh, you mean the one on Sat., May 19, at 4 pm, at The Crossing, at 2548 N Southport Avenue? Niiiiiiiice.
(Well played. I will try to say something witty in person at the meetup so you’re not disappointed! But I could just end up slurring…)
ktfran April 27, 2012, 10:10 am
Yes, I forgot to add the details. Thanks!
We’ve met, so you’re good. I might have to start drinking immediately after the tutoring picnic, so we might both be slurring our words.
jlyfsh April 27, 2012, 10:03 am
i wish i lived anywhere near chicago!
Lolo Sinks April 27, 2012, 11:29 am
Sounds fun! I mostly creep on the site and don’t post a lot, but a Dear Wendy meet-up would be fun. Maybe one of these times when I feel like driving from Champaign. 🙂
AndreaMarie April 30, 2012, 10:05 am
HAHAHA…I did that once…had a major crush on a guy I worked with…we all went out…a few scotchs later….Well we know how this ends. Only issue is he wasn’t only my boss…but my boss’s boss…basically everyone’s boss. He was the head of our department for the US. Even though I wanted seconds I knew I couldn’t because that would be career suicide!!
But now that I am not longer working there…and neither is he….we meet for the ocassional “business lunch”.
IDreamofElectricSheep April 27, 2012, 9:23 am
LW1: “Or what’s done behind one closed door shouldn’t be surfaced through to another?”
What? Wow, maybe you should spend more time learning how to write.
Leroy April 27, 2012, 10:07 am
The backdoor of love if for deliveries only.
theattack April 27, 2012, 11:58 am
Wow, that’s pretty… adventurous. I’ve heard people say “exit only,” but “delivery only?!?!” Wowwwzers
Leroy April 27, 2012, 12:33 pm
Not everything is ass humor!
If you close the door to your heart, the cat burglar of love will climb in through the window to your soul.
Leroy April 27, 2012, 12:44 pm
If you block the chimney to the furnace of desire, you’re gonna get squirrels.
PFG-SCR April 27, 2012, 1:34 pm
Sounds like someone started the weekend drinking a bit early.
What other words of wisdom do you have, Leroy?
Leroy April 27, 2012, 4:35 pm
I’m not ever drunk yet. Though I’m out of wisdom. Those were inspired by a very boring meeting and I only shared them with you so that I didn’t have to say them out loud.
ReginaRey April 27, 2012, 9:27 am
LW 1: I don’t mean to sound incredibly patronizing here (or maybe I do…), but are there REALLY human beings on this planet who genuinely don’t know whether or not “having a secret sugar daddy on the side” is cheating??
I’d like to continue on with a host of snarky comments, but I’d rather the LW get at least a tiny bit of helpful advice…so here it is: Go to therapy, LW. Go to therapy NOW. I’m afraid you have may missed some VERY critical relationship lessons growing up, and I’m also afraid that there’s a critical part of your work ethic (not to mention self-respect) that’s missing…if you’re so willing to sell your body for a bit of financial support.
LW 3: This is classic, really, the whole “still holding a flame for my first love.” But here’s the truth about first loves — The only reason they’re special, or different than any other boyfriend you had, was because you learned what love was with them. The misleading thing about first love is that it’s not any better, really, than love you’ll have later on. It’s just more…intense. You’ve never felt this way before, and it’s basically like being high, all the time. You’re so revved up on all that oxytocin, you think “OMG! Nothing will ever compare to this!” Except, it will. And in fact, it will be better later on, because you’ll mature and grow and you’ll have a deeper, more meaningful connection with someone else. And even more honestly — Your ex really didn’t have all that much to do with it. Yes, you fell in love with him. But you also fell in love with love, itself. I’d even hazard a guess that most first loves, especially those that end (and the vast majority do, in fact, end), are about equally tied being loving the person and loving the feeling of love. All this is to say — Your ex should be left in the past. There’s no sense in moving backward, when you could be moving on to bigger and better (and more mature, deeper) loves.
Nadine April 27, 2012, 9:32 am
eh, selling your body for financial support doesn’t mean she needs therapy. But the situation she has posed here – has committed boyfriend and is presumably in monogamous relationship and in order to do sex work would need to cheat on him – then yeah she hasnt really thought this through.
ReginaRey April 27, 2012, 9:34 am
I mean, maybe she doesn’t NEED therapy…but at this point, I’m not sure what else to suggest to her that may be helpful and proactive. So therapy it is!
Nadine April 27, 2012, 9:40 am
Fair enough 🙂
cporoski April 27, 2012, 9:42 am
Maybe the LW should watch almost any romantic comedy and decide between the rich distant guy or the loving poor guy.
Flake April 27, 2012, 9:34 am
How about that, LW1 gets the Sugar Daddy, and then wisely invests that money into therapy to find out how in the hell that question even formed in her head….
ReginaRey April 27, 2012, 9:39 am
PS, LW 3: My first love was a real doozy. I was 17, almost 18, and about to graduate high school. I wasn’t physically attracted to him at all. He was short, and I often thought, before we started dating, that he could of looked like an alien. But then he admitted he had a crush on me, and asked me to prom, and I quickly fell in love with someone else loving me, which eventually led to me loving him for real. Except, of course, we had little in common. We fought all the time, because we weren’t right for each other, and our relationship eventually imploded in a supernova of DRAMA. But it didn’t matter! Being in love was SO AWESOME. And NO ONE ELSE IN THE WORLD WILL EVER MAKE ME FEEL THIS WAY. So we got back together and broke up a few more times. Eventually, we broke up for real and I dated someone else who I loved much more genuinely, less borderline-psychotically, and more deeply. So press on, LW, there’s better things awaiting you.
Anyone else care to share their tales of first loves?
ReginaRey April 27, 2012, 9:40 am
*kind of, not could of
Anna April 27, 2012, 9:44 am
You already know the story of my first love. Yep, I am 28 and only been really in love once.
Addie Pray April 27, 2012, 9:48 am
RR, I feel so sad for you. Just because I really, really want you to meet some guy – a neighbor maybe? – who gets your panties wet just by looking at him! (Sorry, I could think of no other words to describe it.) And then I want you to jump him, a lot, over many days, until he moves back home to Ohio. (Mostly so I can feel better about myself for my situation with my neighbor but also for you!)
ReginaRey April 27, 2012, 9:53 am
It doesn’t count that I feel that way about Channing Tatum and Matt Bomer (gay! The nerve of it!) and Henry Cavill, does it? Because damn, I’d be remiss to ever have clothes on in their presence.
Addie Pray April 27, 2012, 9:58 am
If you can get one of those guys alone in the elevator and then drop your pants and go to town, then ok, that counts! Not that I have ever done that. … But come on, we’ve already established that pants are the worst. No one likes to have to wear pants, in an elevator, for example.
ReginaRey April 27, 2012, 9:54 am
lets_be_honest April 27, 2012, 10:01 am
Holy crap. Wow. I would let HIM be my sugar daddy.
cmary April 27, 2012, 4:11 pm
Oh, Henry Cavill. In The Tudors? Toward the end when he’s a mostly decent person again? Or even in the beginning when he’s not.
kerrycontrary April 27, 2012, 9:50 am
My first love was when I was 18 and a freshman in college. I could write pages about it. I always heard falling in love was the best thing ever and it truly was. I don’t know if I’ll ever feel so stupidly happy as I did that semester in college. Unfortunately we just weren’t compatible and we were 18-20 in our relationship so we were also incredibly immature. We broke up but were still hooking up so it turned into some horribly messy situation. It finally ended when he started dating one of our mutual acquaintances. At that point he was still telling me he loved me. blahhhh it was so messy I don’t wanna talk about it anymore! But when it was good it was GOOD. And I was so afraid that I was never going to fall in love again or that it wouldn’t be the same, but RR is right, it’s not the same but it’s a better kind of love.
bethany April 27, 2012, 10:18 am
I met my first love when I was 18- a week before I went away to college and it did not end well. Lets just say that I have about 12 journals (seriously) full of me pining away for him and wondering what went wrong, after things ended VERY badly. It took me literally 8 years to fully get over that situation.
Then one day about 3 years ago he showed up in the lobby of my floor at work, because he was doing business in the office across the hall… Talk about weird!!
CatsMeow April 27, 2012, 10:50 am
RR, my first love was kinda weird-looking too! I wasn’t attracted to him but I thought it didn’t matter because we UNDERSTOOD each other on such a DEEP LEVEL.
He lived right behind my mom’s house, and I was such a stalker that me and my friend made this stupid list of ways that I could “accidentally” “run into” him – most of it was completely ridiculous.
One time his mom caught us making out in his house in the middle of the night and she FLIPPED OUT and was like, “GET OUT! GO HOME NOW!” (We weren’t even partially undressed; it was completely innocent). And I freaked out so bad that I left without my shoes and walked home in my socks.
When he went away to college, I thought I was going to DIE. Ohhhh how could I live without him? Yeah, it was an HOUR DRIVE – barely anything. But keep in mind this was before cell phones, and we seriously had to use phone cards if we wanted to talk on the phone long-distance, so it was a lot of emailing and AIMing. I used to save some of our conversations so I could look at them later. The emails were always insanely long.
Then it kinda just fizzled for me and I started crushing on this other guy and instead of realizing that it was time to break up, I dragged it out. I was kinda mean to him when we finally did break up. I’ve since learned how to be a nicer breaker-upper.
Caris April 27, 2012, 6:56 pm
an hour away is not long distance…. my college is 40 minutes away on bus and i go every day. i have friends that live about 3 hours away from college and they get there every day.
lets_be_honest April 27, 2012, 8:09 pm
Think she means long distance phone calls. Jesus I feel old having to explain this, but long long ago before there were cell phones, people had to use phones plugged into the wall. If you called someone with a different area code, it cost a lot more money.
rachel April 27, 2012, 8:27 pm
Hahaha, she totally meant long distance phone calls, and I guess I’m old too because I didn’t even bat an eye.
Temperance April 28, 2012, 11:54 am
Mine was really similar to yours, except I was 16. I didn’t find him attractive at all – he had a stupid haircut that had been compared to Dumb and Dumber, and he was just not cute. However, I didn’t have a whole lot of male attention, so I immediately started dating this guy, because no one else asked. I liked the feelings, even if I wasn’t always happy. He was a conservative Catholic, which I found out when we had a pregnancy scare, when he told me that he was pro-life, so I couldn’t have an abortion, but he needed to go to college so we had to breakup, too. I wasn’t pregnant, thankfully.
He was a total ass, too. He cheated, with a girl that I KNEW had it bad for him (who he later cheated on, too … you deserved it, bitch!).
kerrycontrary April 27, 2012, 9:47 am
Ahh RR thanks so much for your last paragraph. I agree 100 percent and I’ve tried to explain this to girl friends before when they’ve been going through a breakup, but your explanation was just perfect. The love I have now is so much better/healthier/deeper than my first love, but that first love was so intense.
ReginaRey April 27, 2012, 9:51 am
We usually have our first loves as teenagers, or in our very early 20’s, when we have ALL OF THESE HORMONES that are just COURSING THROUGH OUR BODY and that make being in love SO. INCREDIBLY. INTENSE. You kind of get addicted to it. And then, because *this person* is the one fueling those feelings, you kind of get addicted *to them.* And then you think “No one else will ever make me feel this way, EVER!,” and forget that it probably wasn’t the person in the first place, but your crazy ass hormones. It’s why I get so worried when people say they’re marrying the first person they ever loved, or when people get married really young. I’m afraid they’re still high off of the intensity of first love!
lets_be_honest April 27, 2012, 9:48 am
Ya know, RR, I wanted to keep it anonymous, but no, I didn’t know it was cheating. Do you have to be so mean? Also, I’m LW2 too. If he’s my boss, its def not cheating. At least I was clear on that!
Addie Pray April 27, 2012, 9:59 am
It’s especially definitely not cheating if your boss pays you for the sex!
Morgan April 27, 2012, 9:33 am
LW 1, its a terrible idea. A terrible terrible idea. Gotta admit though, sometimes I think a rich dude willing to pay off my loans and buy me shoes isn’t the worst idea I’ve ever heard.
Did anyone see that new dating website that pairs young attractive people who want to take nice vacations with older rich people (men) who don’t want to travel alone. Basically, it’s sex for vacations. I am ashamed to admit that my though process was first “I mean…if it was somewhere really nice…” And only second, “That is a great way to get murdered abroad.”
MissDre April 27, 2012, 9:44 am
I’d think no matter how nice the destination, it would be horribly ruined by the fact that you have to sleep with the nasty old perv. Maybe he stinks. Or maybe he’s into some really weird kinky shit… Ick. Plus, wouldn’t he sort of expect you to hang around with him during the day? Even just being in horrible company would ruin it for me…
Nadine April 27, 2012, 9:46 am
Ha ha I saw that! And I just wondered whether I’d have to have sex with them constantly during the trip, or just once and then enjoy the trip. Because it would be annoying if you wanted to go see a market or whatever, and the guy was like “No, no, sex now, sightseeing later.”
Muffy April 27, 2012, 3:26 pm
also what if he does this often with different women! diseases…..
Fabelle April 27, 2012, 9:51 am
LW1, I want to pretend you have no idea what a sugar daddy actually is. That’s the case, right? Right?? Because otherwise you’d know immediately that it’s definitely cheating!
LW2, I don’t know, I think any boss/subordinate relationship is bound to be fucked up, even if you’re no longer working for him. It depends on the environment of your workplace, though, so maybe give it a shot (once you switch teams)
LW3, I’m sympathetic to this. I don’t think it’s necessarily a terrible idea to casually reach out, but make sure you don’t get your hopes up about anything.
ReginaRey April 27, 2012, 9:56 am
Personally, I don’t think LW 3 would be writing into DW if her hopes weren’t ALREADY up, you know?
Fabelle April 27, 2012, 10:31 am
Yeah, that’s true. If she’s asking if she SHOULD contact him, then she probably already has some dramatic outcome (like reuniting) in mind.
Sue Jones April 27, 2012, 5:04 pm
Michelle Obama used to be Barack Obama’s boss. I do not know how they navigated it… but it seems to be working….
Addie Pray April 27, 2012, 10:09 am
I’m watching the Today show and they’re talking about Sean Goldman, you know, that kid at the center of an international custody dispute for 5 years between his father and his deceased mother’s family in Brazil? Well, I kind of am in love with the father, David Goldman. That’s all.
Addie Pray April 27, 2012, 10:15 am
Oh he *just* said on the show that he’s engaged, to be married, to another woman (not me). Back to square one, sigh.
lets_be_honest April 27, 2012, 10:31 am
How does the kid seem? I followed that story a while ago.
Addie Pray April 27, 2012, 10:36 am
happy and well adjusted – but god what a nightmare for the father and the son.
Kate B April 27, 2012, 10:18 am
LW1: not only is it cheating, it would make you a prostitute. Not that I have anything against prostitutes, really. They’re business people, too. But, is that your goal in life? You realize you’ll have to move to Nevada. I hear prostitutes make a good living there.
CatsMeow April 27, 2012, 10:39 am
LW1, if you want a sugar daddy then go for it. BUT you have to tell your boyfriend. Not telling him is what makes it cheating. And if your boyfriend’s not cool with it, then you have a decision to make: boyfriend or sugar daddy.
landygirl April 27, 2012, 11:05 am
The first letter has to be a joke, right?
the other guy April 27, 2012, 11:31 am
LW1 – its a good idea, work from home, make big money and wouldn’t even have to get out of bed. If I could have got me a Sugar mummy in my younger days… Sign me up!!
You write ‘committed relationship with my boyfriend’..’same time I’m thinking about having a sugar daddy ‘. Sounds like the commitment bit is more of a guideline than a strong rule so to speak.
My advice, MOA from the boy friend, you are just stringing him along anyway and enjoy your sugar baby years, they will pass very quickly. Leave it to many years and you will need to settle for a ‘Mac Happy meal’ per ‘sexy time’ financial arrangement.
rachel April 27, 2012, 12:36 pm
1. Yep 2. Yep and 3. Yep Wendy covered them all.
And now there’s an ad for a sugar daddy site on here.
Jiggs April 27, 2012, 12:38 pm
To LW with the boss crush: Just make sure if you do end up dating, never never never talk about your job in the context of him rating your performance or what he was like to have as a boss. (ie. What did you REALLY think of me as an employee? I thought you were XYZ as a boss etc.) If he starts to say something about your work performance under him, shut that down politely with something like “I’d rather not talk about how we felt about each other as coworkers, let’s focus on what we have going on now.”
Don’t take this completely literally, of course you can talk about the crushes you had on each other or reassure him he was a good boss or something like that. But stay away from the particulars – in every boss/employee relationship there are times when you’re frustrated with the other party’s actions, and it’s best to leave that out of your new relationship. It just never ends well to talk about job performance issues on either end when you’re dating a coworker or former coworker.
(This from someone who, early in her relationship, had several intense fights with her coworker boyfriend-now-husband about how he didn’t know right from left and it’s ruining her life.)
S.B. April 27, 2012, 1:19 pm
I may sound like the odd one out here, but I think LW#1’s problem is not the sugar daddy idea in and of itself, but with the sneaking around behind the BF’s back. Lying to one’s partner is a relationship killer. That said, a friend of mine dated a stripper/’adult entertainer’ a while back and was fine with her work because of the lack of emotional involvement, so IMHO you and your partner would have to discuss what constitutes ‘cheating’. That said, I think the whole ‘sugar daddy’ thing is a bit sketchier than being a straight-up ‘adult entertainer’, seeing as this person is basically buying your time and attention personally for the long term, rather than an ‘exchange of services’. (BTW, I have a suspicion this may be a cultural attitude– sex work is legal where I live, as long as everyone’s of age and consenting).
Furthermore, LW, I’d have a long, hard think about why you’re considering the ‘sugar daddy’ option vs. waiting tables or whatever. It’s a very squirmy can of worms even if you were single, and if you have ANY doubts, you should leave that can unopened.
rainbow April 27, 2012, 2:08 pm
I agree. I worked as a stripper/’adult entertainer’ once, while I was in a relationship, but I talked to my boyfriend about it before I did it, I didn’t go behind his back. That’s a terrible idea.
JK April 27, 2012, 2:24 pm
I can´t decide which DWer has led a more colourful life, you or AKchic.
You´re both awesome, anyway. 🙂
rainbow April 27, 2012, 2:55 pm
Aww thank you honey =)
BTW, I only lasted 4 days in the job. I mostly did it for the kink and it ended up being incredibly boring, so I went back to programming.
AKchic_ April 28, 2012, 12:50 am
I’d love to meet someone with a life like mine used to be.
Of course, there’s no guarantee that they wouldn’t be bat-ass mental by this point.
A sugar daddy isn’t going to help anything. She will become dependent on this person, and he will know it. If he decides to trade her in for a newer/kinkier/prettier model, well, she is high and dry while he’s still having fun.
BreezyAM April 28, 2013, 10:05 pm
It always baffles me when people say “gee why not wait tables instead?”
Let’s see. I can wait tables and be on my feet all night and deal with jackholes or if I’m lucky get in at some fancy resto place (not bloody likely where I live; those are for PROFESSIONALS with YEARS of experience!) or may the same money going out with some guy for three hours and banging him that I normally would in a week.
I wonder which makes more sense economically? I mean does this seriously escape people? And not all those guys looking for sugar babies are old, nasty, or even pervs. Many of them are just sick of “dating” and dealing with relationship drama and just want someone nice and sexy who is willing to have sex and fun on a semi-regular basis.
lets_be_honest April 27, 2012, 2:54 pm
My newfound pet peeve – Slow day at work combined with a quiet DW day. Someone say something controversial!
bittergaymark April 27, 2012, 5:14 pm
Deep down all women want sugar daddies. Its the basis for virtually every male and female relationship. All of those deriding LW1 on here are simply jealous that they are so deep-seatedly ashamed of their own true inner desire to be somebody’s little sugar baby…
Rachel April 27, 2012, 5:20 pm
That’s silly Mark. Who wants a creepy old rich guy? The trick is to find a young, HOT, rich guy. Geez, you don’t know women at all! ;P
Sue Jones April 27, 2012, 11:36 pm
Young hot rich guys usually have many women hanging all over them … and they only have relationships with young hot rich women, or very hot women…. sad but true. The old ones are the ones who will “keep” a young woman, but really who wants that? I never did…
lets_be_honest April 27, 2012, 6:30 pm
And BGM delivers! Well done.
SweetsAndBeats April 27, 2012, 7:40 pm
Most women just don’t like to think that they trade their time, energy, and yes, bedroom access, for resources. It seems like everyone wants to think that they do things simply because they are unselfish or not thinking about what they can get from other people, but that’s a load of shit. I’d prefer to call a spade, a spade, and stop pretending like we don’t trade resources for resources in our relationships. All humans do it… otherwise our species would have died out before we lost our fur.
SweetsAndBeats April 27, 2012, 7:41 pm
I’m pretty sure that this is controversial enough to spark a convo!
lets_be_honest April 27, 2012, 8:06 pm
I actually dont think it’s all that controversial. For example, lets say I’m so selfless that all I spend my time on is helping others. Aren’t I getting something out of that?
As to bgm’s point, I at no point in my life have wanted someone to take care of me financially. I’ve found the opposite actually, that I enjoy taking care of others (when I can afford to). I’d like to win the lottery though.
I do think many people would love sugar daddies or mommies, but all people? I don’t think so.
Iwannatalktosampson April 27, 2012, 6:03 pm
I was thinking the exact same thing LBH!
bittergaymark April 27, 2012, 9:08 pm
Oh, you know I was only speaking in platitudes to get a rise out of you, LBH.
fast eddie April 27, 2012, 7:30 pm
Just getting signed in
joel April 29, 2012, 5:19 pm
Regarding #1, geez. How is this any worse than cheating on your husband and cuckolding your husband? Or cheating on your boyfriend and cuckolding him? These are legal activities in all states. And, women who do such things are not generally condemned by other women, rather, they are seen as victims of an uncaring husband. And, in a court of law, their behavior will not count against them, generally, in divorce, alimony, or child support settlements.
So, #1, go for it. All you have to lose is your boyfriend, who, you clearly don’t care very much about. Don’t tie yourself to a man you don’t respect.
And about that prostitution slur, think how many women marry for money. Are they prostitutes?
CrazyGaloot April 29, 2012, 8:07 pm
I don’t know if I agree the the “move along after a year and a half” advice. I still think sometimes about my second wife who I divorced 12 years ago. She was bat shit crazy and wild as a Nevada mustang, but I loved her dearly and will never forget her. A year and a half isn’t long enough.
Ken April 30, 2012, 1:04 am
Thoughts on potentially dating the boss…
First, no man ever makes a comment about “looking for a girlfriend” to a woman unless he is hinting strongly that it would be very nice indeed if the woman in question were to become the girlfriend.
Second, unless a woman is crazy/stalkerish, she can rarely go wrong by being open about her attraction for a man.
At the same time, dating one’s boss is a bad idea, in my judgment, for many reasons.
Putting these together, I recommend approaching the boss and saying approximately, “I am thinking of quitting my job, and I’d like your advice. I would like to date you, but I have a rule against dating men I work with. At the same time, I enjoy working with you, so if you are not interested in dating, we can forget the conversation happened and continue on as before. What do you think?”
My two cents’…
Another Whore November 28, 2012, 1:49 am
I have major depression. I have trouble getting up many mornings. I also have health issues with my heart and back that make working a regular job very difficult. I’ve been beaten by boyfriends and nearly killed myself. This ALL stems from sexual exploitation that I endured as a child and never told anyone about – until two years ago.
I once went to a therapist to talk about my issues to be freed of my past, and she said “I won’t tell anyone your secrets unless they include child abuse.” BAM. Just like that – “you can’t help me, then.” No way was I going to go to sit in front of a judge to tell a courtroom about what happened to 12 year-old, flat chested, ballerina, middle-class me. No. So, I chose to just go through life and make the best of it.
I couldn’t hold down a job because of my heart palpitations/fainting or my bad back (I’m very tall and had a nasty fall from a tree when I was young). I also had this major depression and feeling of worthlessness. Keeping a job has always been very hard… but that didn’t stop me from wanting to go to school or to pay my rent. Because my parents worked and made just enough that I didn’t qualify for financial assistance in school, I endured six hours EVERY DAY on city busses and worked a freelance graphic design business. But if my boyfriend came home drunk and decided to hit me or strangle me, then I didn’t get paid so well. My parents didn’t talk to me because I had chosen this boyfriend over them (I was young and stupid).
NOW, though, I am 24 years old, still dealing with my depression, but making the best of every single day. And yet, I still rely upon a sugar daddy. I should note: I have never, in my life, so much as taken a single puff of marijuana, never smoked a cigarette, never done drugs – don’t even take Advil unless it’s dire circumstances. I don’t sleep with many men, just this one, and my wonderful boyfriend. I look in the mirror every day and TRY to justify that I have no other choice, and tried to justify that it’s not unfaithful if I pay my bills and don’t turn to my boyfriend with helplessness in my eyes. I have a semi-regular part-time job, but it’s not enough to pay all of the bills. I’m ashamed, yes, but I’m not a criminal. I want to buy groceries to take care of my man, I want to clean the house, I want to find peace with my past, I want to propose to my boyfriend, and most of all, I want to end my ‘business relationship’ with the sugar daddy. It sickens me. But don’t you dare tell me that I could just “you know, wait tables or something” because if I had not given you some background (and there’s lots more), you would have thought I was some drugged up loser carrying prada and gucci bags around. Don’t you dare judge me, because I am a GOOD person, spending time at the SPCA, organizing events to raise money for charities. I’m a good person.
ra-ra April 28, 2013, 6:15 pm
Shouldn’t have asked for advice then, if you already had the only thing you’d be willing to hear all written up.
Another Whore June 11, 2013, 12:45 am
I’m… not… the original poster? I’m “Another Whore”.
I’m angry that this girl is asking for advice and she is being judged by a bunch of menopausal women. She asked for advice, not judgement. Shame on you all.
sugar baby September 12, 2013, 8:53 pm
Wendy you are way off the picture here, I am a sugar baby with a boyfriend! Yes he knows and yes he’s in support of it as it helps me pay MY BILLS and MY TUITION. It is a job like any other one. No you don’t have to have sex to be able to be a sugar baby. Misconceptions are all around and it seems to me hating on women who go out and get what they want shows jealously.
So to the girl above if you feel you have a solid relationship and he’s open to you being on outing’s with older men. Then go for it. Tell him as I did it’s nice to have the support and when you start actually going on potential dates with a SD you have someone watching your back. Please always carry mace and tazer as there are creeps out there. Do your research before you jump. Good luck and don’t listen to all the judging just brush it off.
SkyeCat October 19, 2013, 6:09 pm
So what if you already have a job and work your *** off and unsuccessful at finding another one and need the financial help. I’m in the same boat as original poster. I have a boyfriend but we are both suffering financially. My parents only sometimes help me with my financial problems. All other time i end up forfeiting food money or gas money to pay my bills because I don’t always make enough at my job. I haven’t talked about getting a SD with my bf yet but I really think it would help us both.