Updates: “Issue to A Dress” Responds

It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing now. Today, we hear from “Issue to A Dress” who was surprised that a friend still expected her to pay for a dress she agreed to purchase from her after she gave her a concert ticket worth the same amount. Keep reading to see whether she paid for the dress after all.

I definitely don’t agree with your advice; however, I understand your point. I did pay her exactly for the reason you stated — for my boyfriend and his roommate’s friendship. I was 100% the bigger person here. She emailed me horrible things following the initial miscommunication and she freeloads off everyone in my boyfriend’s townhouse, including her own boyfriend. I, for one, do not expect free hand-outs and that is exactly why I did pay for the dress. I would never take a ticket from someone and not offer them anything. A drink, money, pay for parking, that just seems weird to me. I am lucky enough to buy expensive things, because I work very hard, so I found that really rude/offensive, but it is your opinion.

I appreciate your response and it is very interesting to read what others have said.

I’m gonna go out on a limb here and assume the two of you probably won’t ever go to a concert together again, although I bet you’d both be terrific company.


If you’re someone I’ve given advice to in the past, I’d love to hear from you, too. Email me at wendy@dearwendy.com with a link to the original post, and let me know whether you followed the advice and how you’re doing now.

You can follow me on Facebook here and sign up for my weekly newsletter here.

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


  1. Way to get defensive, LW. I still think you were in the wrong.

    1. Yeah, I agree. Unless the two of them agreed beforehand that the concert ticket was re-payment for the dress, the LW doesn’t really have a claim here.

  2. If you think she’s a freeloader, I don’t know why you would expect anything in exchange for the ticket. I guess you can just think of the money as the price you paid to learn that you don’t really want to be friends with this girl.

    1. i was thinking the same thing after reading this. if you know she has a history of doing this, why go in to a deal like this with her?

  3. I actually disagreed with Wendy and most of the commenters on the initial post (and thought the title given to the letter was a bit harsh), but I’ve gotta saw, LW, you’re not going to win any supporters with that response. It paints you in a very negative light, and makes your look uber defensive and like a bad communicator (which a lot of commenters pointed out with the initial letter).

    1. Avatar photo Addie Pray says:

      The title given to the letter was Should I Pay for the Dress, or something close. How is that harsh? That’s what the LW asked Wendy to answer….

      1. i think “issue to a dress” is a hilarious, hilarious pun. i didnt even get it until way after i read the letter… lol

      2. Avatar photo Addie Pray says:

        Ha, I just got it too and commented as such – below.

      3. OHHHH I get it now! I’ve been really slow today. Sheesh.

      4. I think it was actually, “Should I pay the money I owe?”

      5. Avatar photo Addie Pray says:

        I might agree with you if the title had been: “Should I pay the money I owe, even though I am a dumb idiot”

        Yes, dumb + idiot

        Now that would be harsh.

  4. If you say that you are going to pay for something, you keep your word and pay for it. It’s important to actually DO the things that you say that you will do because otherwise no one will trust you. Endeavor to be a trustworthy person LW.

  5. lets_be_honest says:

    Wish she’d answered some of our questions.

  6. No need to be defensive. Just treat it as a lesson in clear communication – particularly since you knew she had a history of freeloading and didn’t have the same values over money as you did.

    And did someone judge you for a $95 dress or ticket? I don’t remember that but you are right – you are entitled to whatever you can afford without apology as long as you come by it honestly.

    1. I said she was lucky to be in a position to afford pricey things. She took that a judging her. Was not judging at all — just pointing out that since she doesn’t have to worry about money… maybe she shouldn’t worry about money and just count her blessings.

    2. Yeah, I don’t remember anyone judging her for that, either.

      1. Well, it doesn’t really mean she doesn’t have to worry about money at all. I sometimes buy fancy stuff, and other times I can barely feed myself. But I also have terrible money mangement skills. I just don’t care enough about being broke, because I know it’s only temporary. (My terrible money mangement is also limited to everyday spending/paying bills on time, I got the big picture stuff taken care of (pension fund and life insurance ftw!)

        My point is, even if she can afford those tickets, she may not be able to just write them off. Not saying anything to the right or wrong in this situation though.

  7. Avatar photo bittergaymark says:

    Seriously. Yikes. What a defensive bitch… She sounds like a real joy to be around. Get the fuck over yourself already. You WERE wrong. And if you don’t see that? Eh, good luck with life…

  8. Avatar photo GatorGirl says:

    LW, I get where you’re coming from. I agree your update was worded a tad too strongly, but I totally understand your frustration. Chalk this up to a BIG lesson learned.

  9. Grilledcheesecalliope says:

    I also disagreed with the advice, but hopefully LW you learned something about clear communication. Some people are spoiled which it sounds like the gf is and you have to make it clear when you expect them to pay for things. Paying her was the right thing to do to keep the peace.

  10. The thing you’re forgetting is that you DID get something in exchange for paying for her concert ticket: someone to go to the concert with! I know plenty of people, women in particular, who aren’t comfortable going to events by themselves. You say that you were looking for someone to go with at the last minute, presumably because the person that the ticket was intended for had to back out or because you waited until the last minute to find someone to give it to. The fact that you gave it to your boyfriend’s roommate’s girlfriend, who you don’t seem to like very much, makes me think that she was your guest of last resort. If she hadn’t taken the ticket would you have gone alone or, like a lot of people in your shoes, been too uncomfortable with that and just stayed home?

    Even if the above scenario isn’t accurate, I can see how this girl may have assumed that this is what happened. In her mind, maybe she was doing you a favor by giving you someone to attend the concert with so you could go yourself! Or maybe she thought that (god forbid) you were doing something nice and giving her a ticket when the person who originally planned to pay for it fell through. She might be super ungrateful and spoiled, but in this particular case I still have to side with Wendy that you shouldn’t have assumed she would pay for the ticket. Maybe YOU would always offer to pay for such things, but what’s “normal” or “weird” for you isn’t always the same as for everyone else.

  11. Avatar photo Addie Pray says:

    Yikes, defensive much?

    In other news: I just got this – the signoff name was “Issue to A Dress”! Get it? To ADDRESS!!!! AND IT WAS ABOUT ‘A’ ‘DRESS’! Hahahahahaha clever!

    Oh sssssure, like you all got it right away.

    1. I’ll own up to not getting that until I read your comment! I think my brain is frozen today!

  12. lets_be_honest says:

    Clearly the lw was born in the 80s.

    1. Avatar photo Addie Pray says:

      Bwahahahahaha, so obvious. And clearly she’s the *oldest* child. Kidding, Gator Girl, keep your pants on. Haha. 😉 Lw is obviously the baby. Can you think of anything worse? Being the baby of the family *and* being born in the 80s? Like, no good can come from that birth. … K I D D I N G. It’s “be dramatic” day.

      1. Avatar photo GatorGirl says:

        you’re too much AP. Also I’m not wearing pants, TMI?

  13. Funny response, Wendy! (You, not the LW.) Love it.

    1. Avatar photo bittergaymark says:

      Yes, it was so wonderfully pithy, I loved it!

  14. LW, This is a lesson that you need to have clear, frank conversations when money is involved. I know it can be awkward or trying to joke. You will have these kinds of miscommunications over and over again if you deal with money so cavalier. You work too hard for it to let these things go.

  15. “…she freeloads off everyone in my boyfriend’s townhouse, including her own boyfriend.”

    Well, at least I can say I was right about there being issues under the surface! But really LW, how does one freeload off her own boyfriend? I would imagine he’s the one who invites her over all the time?

    “I am lucky enough to buy expensive things, because I work very hard, so I found that really rude/offensive”

    I don’t get this—found what “rude/offensive”? The suggestions in the original letter that indicated yeah, sometimes friends just give each other stuff? I’m just confused as to what provoked your very defensive response. But at least you paid her the money, I guess.

  16. You know, I actually know this LW quite well. I can see that she didn’t do a good job of explaining herself here, but you guys are way harsh. She’s a really nice person who got caught up in a tough spot and was genuinely upset about the response from Wendy and all the commenters. This update was defensive, but it also shows that she did exactly what you all said she should do. It might do you guys well to take a deep breath before you start calling names.

    1. As far as I can tell, only one person resorted to name calling, which I agree is completely inappropriate. However, I’m assuming the LW reads the site somewhat regularly, and if so, she’s already aware of that particular commenter’s general disposition. If not, please tell her to rest assured, it’s nothing personal.

    2. I think most people are just confused about the level of her defensiveness— I didn’t see anybody (besides, yes, BGM…) call her names.

      1. Avatar photo bittergaymark says:

        And I absolutely DIDN’T call her any names until this absurd update. In fact, my response to the initial letter was perhaps among my most measured… This LW (however nice she is) has been wrong now. Twice. First with her problem to begin with and now with this hilariously defensive update. Look, if you can’t take criticism well, don’t ask for. Please.

      2. I know, I was specifically referring to your comment on this update (and I only name dropped you as the one exception to my assertion that NOBODY was calling the LW names— just trying to cover all my bases so the poster didn’t come back like, “But Mark did!”)

    3. Really? I just skimmed over the original letter and responses and I didn’t think it was particularly harsh. Anyway, every LW should know that defensive updates get DWers all riled up, amirite? 😉

      1. lets_be_honest says:

        Not seeing it either. Is she pissed she didn’t get the answer she wanted? She got an answer to her question. Isnt that all she wanted?

  17. Geez. I was sort of on the fence about this initially. I could see where the LW was coming from, but also realized that she probably should have been more upfront with the roommate. Considering how minor of an issue this is compared to the other stuff we hear about (cheating, lying, etc.), I don’t really know why there’s so much rage over it. A lot of people commit faux pas when it comes to stuff like this, so I don’t think it automatically makes her a bitch or “bad company.”

    1. I think the same thing too. I chalked this up to a 95$ lesson that the roomate’s gf was someone to watch out for. I knew a girl like the gf in high school who claimed I didn’t pay her for some alcohol – which I in fact did by buying the next round (this is back when I was 16) and she shouted “you’re just going to steal money from me for alcohol” right in class and I was so embarrassed at the time because I know the teacher heard. Anyways, watch out for these people LW. They suck.

  18. It seems like the LW wanted Wendy to endorse her feeling that she should not have to pay. However, if you took this to Judge Judy, she’d note that the LW clearly offered to write a cheque to pay for the dress. Case Closed.

    It doesn’t really even matter how the concert came up, because the offer to pay in cash (well, cheque) not trade existed before all that. But even so, when you invite someone to join you at an event, that is not really the same as offering to sell someone your ticket. So, unless there was an explicit request by the LW to substitute the ticket for the cash, which was then accepted by the other person, sorry, you’re SOL.

    The real lesson here is never enter into any financial arrangements with people you are not sure about, never loan money you can’t afford to throw away, and never expect others to pay for your mistakes.

    And seriously, being offended because Wendy suggested you are well enough off that you can afford not to let this bother you? So you let both the money and Wendy’s remark bother you. You want to be offended, so enjoy it!

    1. Haha, yes, love the Judge Judy reference. I can just imagine it

      Judy: Did you tell her you would pay?

      LW: Yes, but..

      Judy: Then pay!

    2. Haha, I was also wondering, “What Would Judge Judy Say?” when I read the original letter. I’m pretty sure JJ would tell the LW to pay, and she would have been way harsher than the rest of us.

      1. My fave JJ expression is “your looks will fade, but STUPID is forever.”

      2. I love judge Judy.

      3. hahahahah, oh man I love her. She does NOT put up with any foolery.

    3. I agree about being invited doesn’t always equate to buy the ticket. I had a good friend invite my husband and I to a baseball game because they had an extra set of tickets. After we agreed to go, and far closer to the event, my friend casually mentioned, oh the tickets are such and such a price when you get a chance. We paid, but it seemed like something that should have been brought up from the start. Like hey, our friends can’t use these tickets, want to buy them and come with us?

      And Judge Judy would be all over this!

  19. OBVIOUSLY, the LW DID in fact spring the whole “exchange” thing on the other girl when they were already on the way to or from the concert. She would have clarified that in her very defensive response if that had not been the case. So I think now it is more clear than ever that LW was in the wrong.

  20. Wait…it seemed weird to you that this chick, a well-known freeloader, didn’t offer to pay you for the ticket, or drinks or parking? Why? If you knew she was a freeloader, then wasn’t she just continuing to act in the same manner she always has? I’m confused.

  21. Funnily enough, the advice could’ve been applied to the roommate’s GF had she been the LW, since she’s apparently going around buying a bunch of clothes she doesn’t even know fits her.

  22. Regina Chapman says:

    Oh Wendy, how I love your understated responses.

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