Quickies: “Should I Spend New Year’s Eve with My Friends or My Boyfriend?”

For New Year’s Eve my friends and I want to go to a party so we can dance and have fun, but my boyfriend wants me to spend it with him and his friends at his home, which I think is kind of boring because, instead of dancing, we will be drinking and I don’t know his friends that well. I tried to convince him to come with me (my friends want that too) and he said he will but he will not have fun because it’s not his kind of party and, of course, that will make me feel bad. He was also saying that it would be better if we party in our own ways and see each other the next day, but I don’t want it like that.
I don’t know what to do. Can you help me with some ideas? — Stumped on NYE

If you think hanging at your boyfriend’s home on NYE sounds boring because you won’t dance and you don’t know his friends that well, then dance… and use the occasion to get to know his friends a little better. Why wouldn’t you be able to dance in his home? Just turn the music up and let loose. Suggest to your boyfriend that you spend the earlier part of the evening at his place, cooking and eating a delicious dinner all together (or ordering out, if that suits you more), and then, after you’ve all hung out there and pre-partied for a couple of hours, head to the party you and your friends want to go to and ring in the new year there. If the two of you can’t get over yourselves enough to compromise on this and each spend a little time doing something on NYE that isn’t necessarily your first choice but that makes your partner happy, then, yeah, just party in your own ways and spend the next day together. What’s the big deal? It’s only one night. Really, people put too much significance on NYE. Just remember that whatever you decide to do, don’t drink and drive.

I’m a gay man with a boyfriend I love. I can feel that he loves me too. Even though I love him a little too much. I have given him lots of thoughtful gifts, but it seems he rarely reciprocates. It’s not like he has never given me anything — the ratio is more like 3:2. But I always pay more. I’m 22 and don’t have job. I’m a student. My dad gives me pocket money and our financial situation is not stable right now. I have told him about this before. He’s 23 and has a job. He can totally afford to pay for himself and for me from time to time.

I have been observing him since our first date. He has been very tight with money. Whenever we go to a restaurant or to the movies, most of the time he just waits for me to take out my wallet and, the minute I do, he won’t stop me and I end up paying for both of us. I’m so sick of this. It’s been taking a toll on my mental health. I feel hurt and used. I’m a nice guy. And I love him. And I don’t want to play games with him or tell him explicitly what I don’t like about him. All I want is for him is to chip in a little and pay 3:2 (3 being the frequency he should pay since he has a job and should pay more) or 1:1, at least. Am I wrong to be thinking like this? Please, I need some advice on how to deal with this situation. — Dating a Cheapskate

If the ratio of your spending doesn’t suit you, adjust how much you’re investing on dates and gifts. Or get a part-time job so you don’t have to rely on your financially unstable father to give you pocket money (you’re 22, for Christ’s sake, not 12!). Or suggest activities that don’t cost very much, if anything. Movies and dinners out get expensive and for a couple of guys in their early 20s, one of whom is a student with zero income, there are plenty of things you can be doing together that hardly cost anything. (Here are 52 cheap date ideas to get you started). Don’t blame your boyfriend for not keeping up with the spending ratio that YOU decided was appropriate. He may have expenses and bills you are unaware of. Or, he may be saving for something. If you don’t want to play games, be honest with him and tell him that, without a job, you can’t afford the kinds of dates you’ve been going on, at least when you pay for you both, and would he mind doing things together that don’t cost as much. Maybe that will be the nudge he needs to start treating more often, or maybe he’ll be relieved that you’ve decided to be as budget conscious as he is.


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


  1. LW1: I feel for you. Every NYE for the past…10 years I think?…I’ve hosted my friends. First at my parents’ house, and then at my own place. Last year things just didn’t work out — specifically, my friends got sick. I was really bummed, but at the same time my (at the time fairly new) boyfriend asked if I wanted to go to a swing dance (his uncle is a trumpet player in a semi-professional jazz band). Usually I prefer to stay in, eat too much, drink too much, play board games, and hang out in sweat pants so I wasn’t sure, but since my friends weren’t able to come over, we got dressed up and went to the swing dance. I actually had a really great time! I got my very first New Year’s kiss at midnight, we talked and laughed a lot, wore ridiculous New Year’s hats and tiaras. It was really fun. I love Wendy’s idea of compromises on both ends. If you follow that I think you will both be satisfied.

    1. And LW2, I think this is a difference of expectations/difference of Love Languages. It sounds like you tend to show love through gifts, but your boyfriend doesn’t, which is pretty common. I would sit down and have a conversation about it, and about money management. Explain to him that you can’t foot the bill all the time and if you two keep on going out to restaurants, movies, etc. you can’t pay for it all. If he’s completely unwilling to compromise, it may be time to think of moving on. (Keep in mind though he may have bills that you don’t — student loans, credit card debt, etc.) A good money conversation now could help you become closer as a couple.

  2. Laura Hope says:

    LW#2 My husband’s a mathematician. I’ll have him work up the #’s / ratios/ projections. Seriously, dude, tell him how you feel. Maybe he’s more interested in saving for your future than having expensive dates. Or maybe he’s just tight with money. Or maybe stinginess is a reflection of his character. You guys need to talk.

    1. The difference between a 22 year old who gets “pocket money” from his Dad and a 23 year old who pays his own way in the world is a huge difference. Mr 23 may have a job, but he is not likely the CEO of a major company at this point, and he may have rent and bills to pay that Mr 22 does not. And even if Mr 23 is still living at home, he may be saving to begin his life as an adult, get his own place, etc. You are right that the first point is communication. But the second one may well be that M. 22 has some growing up to do. LW2, if you feel cheated then make things more equitable, on your own or through talking. But when you buy things or meals for your lover, you don’t keep score. That’s what “gift” means. If you weren’t doing it because YOU wanted to, then why are you?

      1. Definitely agree. When I was in my first year out of college, real life hit me HARD. That first student loan payment came much quicker than I had anticipated.

  3. LW2: Communication is the single most important thing in a relationship. More important than attraction, than sex, than love, than anything. If you can’t talk to each other, then nothing you mentioned in your letter matters, because your relationship is doomed.
    I know that sounds blunt, but it’s the absolute truth. If you can’t talk about trivial things like who’s paying for dinner, then how the heck do you talk about the important stuff?
    Next time you see him, talk about the paying for dates thing. Get creative. Use Wendy’s great suggestions for less expensive things to do together.
    You wouldn’t have any trouble talking about this with a friend, right? So you shouldn’t have any trouble discussing it with him. I know, it’s scary, what if he gets mad, what if he doesn’t want you anymore because you don’t want to pay for dates all the time, what if……..
    I’ll tell you what. He’s probably going to be relieved that you brought it up, because he’s probably been feeling awkward about it too. 🙂

    1. Yeah, I’m not sure why LW2 hasn’t just talked to his bf about this. It would be a simple as saying, “hey, money has been a bit tight, so I need to cut back on my spending. How about we stay in?”
      My question for LW2 is, who is the one suggesting these dinners and dates? If you are asking your bf out then it isn’t totally unreasonable that he would expect you to foot the bill. If he’s asking you out and then expecting you to pay, that’s a different story.

      1. I really didn’t think of this at first, but you are right, if the LW is the one that always wants to go out, then I think that would be where the confusion would be with who is paying.

  4. Avatar photo Addie Pray says:

    Does anyone like NYE? Everyone I know hates it – and all the hype, stress, expectations, and expenses that come with it.

    1. I love it. New Year’s is probably my favorite holiday. I love the chance to start fresh in a way, and I really love the uninhibited celebration that goes with it. Like I mentioned above I have usually spent New Year’s Eve in a low key setting at my place with friends over and we basically eat, drink, and be merry. We watch movies, play board games, drink too much wine and champagne, and eat too much, but it’s fantastic and really fun. Last year was fun in its own way too, but I have to say, I LOVE my friend NYE parties.

      1. Avatar photo Addie Pray says:

        I’ve had pretty boring NYEs. (Well, I’ve just not had the typical “big deal” NYEs.) I think it’s because I’m often taking advantage of the days the office is closed to go away and visit family without taking vacation. Oh fun game, let’s go back and think of how we’ve celebrated NYE pasts:
        2013: I was in Rio with my nephews drinking champagne with my brother’s in-laws on a beach
        2012: At home fighting with my ex-boyfriend b/c he got mad b/c I had had wine at brunch earlier that day and was apparently trying to sabotage our NYE plans together by getting day drunk (I wasn’t even drunk! and it was all worn off by 2 pm!)
        2011: you know what, this game isn’t fun. haha.

      2. My sister is getting married this NYE, so M and i have to travel down dubious icy northern Saskatchewan roads in the middle of winter (it was -47 with the wind chill this morning… I mean, seriously is that even a real temperature?) You know how they say, “out in the sticks”? Well, Meadow Lake, SK, is well out past the sticks into the f’ing tundra. I mean, i’m happy for my sister, but who wants to be out there for NYE? Rio doesn’t sound so bad.

      3. Avatar photo Addie Pray says:

        Oh man that sounds brutal. So, up there does everyone drive big ole honka trucks so you can navigate those snowy/icy roads? I feel like my Prius wouldn’t make it far.

      4. I have an SUV now (which actually gets better gas economy than any of my cars except the ol’ 86 Chevette, for the benefit of any Prius owners), but before that, you just drive for conditions. but it’s still scary, deer all over the road, no one around if you get in trouble. It’s a lot better now that there is decent cell phone coverage, but you still shouldn’t be on the road without a proper emergency kit including extra blankets in case you get caught out.) But then again, i’da probly gotten a bad sunburn in Rio, so, yeah, this is better…. [doesn’t believe what he is saying, not one bit]

      5. Oh my gosh – is that approaching absolute zero?

      6. Oh I remember your creeper ex! Yikes. I think NYE in NYC would literally be my worst nightmare as an introvert who loves her space. I’ll watch it from the comfort of my own home while wearing yoga pants and gorging in taco dip and champagne with friends.

    2. shakeourtree says:

      NYE is my second favorite holiday. (Independence Day is #1.) Everyone is usually back in town after visiting family over Christmas, so it’s nice to spend a holiday with my friend family because they are a lot less dramatic and a lot more entertaining than my actual family. And most everyone gets New Year’s Day off, so it’s one of the few times a year that everyone with all their different schedules can get together. And THEN I get to do my all-time favorite activity–that is, dressing classy and acting trashy. So much champagne! So much dancing! So many sparkles!

    3. I hate it. I feel like there’s a lot of pressure to “do something”. Last year we had a 7 month old and we didn’t really want to go out, but we ended up going to a house party. It was fine, I guess. I’d have rather been at home with my husband, with our son up in bed. I imagine this year will be more of the same.
      Where I grew up there aren’t really any good parties, and that was where I was all through highschool and university, so I never got into the idea that it was fun to go out and go crazy. I’m not a go crazy kind of person anyway, so having the pressure to do it just makes it even worse.

  5. Laura Hope says:

    I was a bartender for years. Always had to work on NYE and watch everyone partying and having a great time while I was working incredibly hard for very little money (people don’t tip well that night–maybe they think it’s all-inclusive). Anyway, when I finally had the freedom to go out, I had a boyfriend who hated to go out and since I chose to be with him, I never got to have that perfect night. Boo hoo, right?

  6. Laura Hope says:

    Oh, the moral of my story is to be sure to tip your servers!

  7. Laura Hope says:

    One time I worked a private party for The Clash which went till 4AM (after a concert) and they didn’t tip us. I guess they thought the hotel was covering it but na ah.

  8. jilliebean says:

    LW #2, if you’re not comfortable saying anything directly, just operate under the assumption that you are sharing the costs of going out. So when the bill comes in the restaurant, take it, do the math and say “ok so we each owe $22.50” or whatever it is.

    As far as presents go, that’s an easy on as it’s fully under your control. If you are buying more than you want to – stop.

  9. I don’t get it, if you want to spend money on someone by all means do that, but don’t expect that they have to spend just as much money on you. This should be a wake up call to you to start being smarter with your (I mean your dads) money. You should take a page out of your boyfriends book, and learn how to save your money so one day you can be financially independent like him. As for the dinners, if this is a serious relationship, you really should have no problem discussing where and when you want to go out, what you can afford, and who’s paying. My wife and I pretty much go out to eat twice week, and she always lets me know how much she has wants to spend, so we can decide from there where we want to go.

  10. LW 1, just go out with your friends. Sure, it makes sense to compromise with your S/O for SOME events but you can do that the other 364 days of the year. Spend NYE separate, have a good time, and go out to brunch with him the next day to compare notes about your nights. There is nothing wrong with doing tbat.

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