Boyfriend +1 | The Roommate

The Situation:

I am in grad school in the south, and my bf lives in Boston, so we’ve been doing the long distance thing since the fall. Here’s my situation: I have a summer job in Boston. It’s unpaid so the only place I can afford to live is at home (I am from Boston also). My bf and I want to spend as much time we can together over the summer since it is hard during the school year to do so. The problem is, he has 2 roommates, and while we’ve discussed that we want to spend every (or most) nights together, I feel weird about basically moving in with him and his roommates and not contributing. I have no income since the job is unpaid and any income I have will be going towards my loans. We could stay at my parents house some of the time, but for the most part, we will realistically be at his apartment and I’m going to need a key. His roommates both have gf’s too and both usually sleep at their gf’s apartments. I get along well with both roommates- and I spent every night of my 3 week Christmas break there and one of them commented on how fun it was having me (not a shock because I clean up the kitchen from time to time and helped him edit his grad school essay). I just don’t know what the right thing to do is. Can I stay there with out contributing to their rent? It’s a small apartment and I don’t want to be a “squatter”. Or are we both over-thinking it, and the roommates just have to understand and deal with the situation for 3 months?

As long as you act respectfully and get along with the roommates, there is no reason why they would have a problem with you staying there. Since your BF has no reservations about you staying there again, I assume your boyfriend didn’t get any negative feedback from his roommates following your previous stay. Forget the monetary contributions. Don’t hog the living room TV, leave clothes everywhere, or monopolize the DVR and everything will be alright.

It sounds like your BF’s roommates understand your situation and really like you enough to not make this an issue. Obviously you wont be able to contribute to rent but if at all feasible, get groceries every now and then. They are guys so they will definitely appreciate this and it will probably make you feel a little bit better about the whole situation. Pitch in when and where you can and I’m sure this wont be an issue—especially if they stay at their girlfriends place’s most of the time!

Yeah, this is really straightforward. Just don’t be a pain in the ass, and it will all work out fine.

I agree 100%. Do small little things that will help out around the apartment and no one will care.


“Lets just be friends”

The Situation:

So I’m dating this guy. Well, a few guys. But one of them in particular has me asking “What’s the move?!” We know each other through a mutual friend (his BEST friend, my good friend). We’ve gone out a few times and had a GREAT time. We get along perfectly. He’s done everything right – called and texted appropriately, complimented me, and acted chivalrous and respectful. Sounds like Mr. Right, right? Wrong. Though he’s a handsome guy, I’m not feeling the sparks. Out of respect for our mutual friend and the fact that I think he’s a great guy, I want to be upfront with him about “just being friends” (and he would make a great friend). And I’d like to minimize the awkward factor for both of us. How do I let him down easily? What’s the move?

I am putting your chances to become legitimate friends with this guy somewhere around the likeliness of Karen letting me have a threesome with her. You and me can just keep on dreaming. If the guy is into you (which it sounds like he is), he will pretend to be your friend so he can sex you in the future, and if he is not into you, he’ll just never talk to you again. Either way, there is no real friendship in your future.

The play here is to let him down gently without creating any extra animosity or awkwardness in the process. My advice is to play your “fade game.” Don’t initiate contact, make excuses why you can’t hang out and basically fade away. And that’s all you can do. If you want to make friends, don’t date them first.

The first thing you need to do is stop going on dates with him and slowly make what your relationship is now, more of a friendship. After a few, “Oh I’m sorry, I cant!” responses to his date requests, I think you should have the Let’s Just Be Friends conversation with him. Unfortunately, I don’t think there is a way to truly get out of this one without it being slightly awkward for the both of you. The most important thing is making sure your mutual friend doesn’t feel the effects of this afterwards.

We are both pretty much describing the fade game. One thing I should add is that this guy may want to know why things changed. The farther you’ve gone with him physically the more likely he is to be confrontational about you blowing him off.

I agree that you need to go into this assuming this guy is very into you and will react in a way that shows he is hurt and upset. For the sake of your friend, I think a conversation needs to happen even if you do play the fade game so there is no confusion about your status. You need to be as clear as you can about what you are looking for.

Office Romance??

The Situation:

I am hoping that you can help me out with my internal struggle of whether or not coworkers should be off limits in the casual hookup pool. I have recently been out to drinks a couple times with a very attractive woman that I work with. We both work long hours and have stepped out for a couple of drinks late night. She is definitely a cool and fun person, however, I have no interest in dating her. I am not sure where she stands on the issue. I’m wondering if I should just go for it and hope she is on the same page, worry about repercussions later, or avoid the entire episode so as to not complicate things at work.

Point your weiner elsewhere. You acknowledge in your letter that this will probably blow up in your face and the last thing you want is an awkward situation with a co-worker with whom you spend long hours. I don’t think it’s worth it. Drinks with co-workers as a group is fine, but if you’re attracted to her and considering going for her just to hook up, I’d stay away from the one-on-one drinks. However . . . attractive girls have attractive friends, and meeting her friends might be a good way to use your co-worker’s attractiveness to your benefit without pooping where you eat.


Definitely avoid the entire situation. Work hook ups can get very messy if it ends up badly. You not only make things awkward for the two of you, but for your coworkers around you as well. If you like the girl and enjoy grabbing a few drinks with her after work, then that’s great, but don’t let this evolve into anything more than that. Luckily it sounds like you haven’t crossed any line with her and I say keep it that way.

I agree with Karen that the “hook up” should be avoided. But I would even avoid the one-on-one drinks after work unless you’re that confident in your self-discipline. And, what if she actually does like you, then you may be in a situation of leading her on, and it could get messy.

Agreed, maybe instead of going one-on-one, you only go with other co-workers so you don’t give her the wrong impression.

Sister(s) | The forbidden fruit?

The Situation:

So I met this girl thru my sister and she’s pretty cool, but not great. We went on a date and hooked up after. Both were marginal at best. I know cooler girls and better hook ups. Truth be told I see this going nowhere but am not opposed to keeping it around with as little effort as possible because she lives a few blocks away. Problem is, she probably won’t put out unless I man up for a second date, but I’m so apathetic to the situation I don’t feel like wasting the time and money but I have nothing else on my plate right now and I always like having something going. She’s a good gal, just not my type of gal and I know I’ll see her again thru my sister so I can’t straight up disrespect her even if I wanted to (plus it would reflect poorly on my sister and the family name). I’m trying to balance this girl’s feelings, my sex drive, my sister’s reputation, and avoiding future social awkwardness. What’s The Move?

First, I think your sister’s reputation will most likely remain intact no matter what happens in this situation. You are an adult and presumably so is this girl (if not we never had this conversation). I don’t think she would hold it against your sister or that your sister would hold it against you if things between you and her went sour. Most relationships do at some point, after all. So you basically have to balance (1) your desire to get laid with (2) the possibility of hurting this girl’s feelings and future social awkwardness with her. Lucky for you, I think in this situation you can have your cake and eat it too. Here’s how it goes – you can have a physical relationship with this girl as long as you don’t lead her on. Hooking up is a two way street. You could always do something in between a booty call and a formal second date by inviting her out to a bar where you and your friends are. This would take the pressure off of a dinner date, but still be way classier than a booty call/text. I think if you invite her out or to meet up while you are out, she may become comfortable with you and you will be able to satisfy all your concerns. You get laid, no one’s feelings are hurt, your sister’s rep will be ok because inviting a girl out to a bar is nothing to be ashamed of, and you won’t have the awkwardness of knowing you booty texted this girl next time you are out with your sis. Basically, you get all four for the price of one! Billy Mays would be proud.

I am assuming that she doesn’t have the same feelings for you that you have for her. With that said, you need to end things before it gets worse. Not only should you never lead a girl on that is into you, but you DEFINITELY shouldn’t do it if she is a friend of your sister’s. Using her because she is down the street and you have nothing else going on is no excuse. It will only lead to disaster. You have two options. #1: you can be honest with her and let her know that you’d really like being friends with her but you just aren’t ready for a relationship or #2: slowly start distancing yourself. I only give you option 2 because you only went on one date and I really don’t think you need to explain yourself to her at that point. It should be fairly easy to give her the impression that you would rather be friends without hurting her feelings. I would suggest #2. Not only will it avoid awkwardness, but she will appreciate you for it and your sister will too. There are plenty of other girls out there looking for a good time that you can “please” yourself with, it doesn’t have to be with your sister’s friend.

I don’t completely agree with Karen on this one. There is nothing really to end at this point. You went on one date. This girl can make her own decisions just like any other girl, and as long as you are not acting deceitfully, I don’t see why she shouldn’t have the opportunity to accept or reject things. If she wants to be wined and dined and you don’t want to, then you go on your way. If she doesn’t mind meeting you out and then hooking up, I see no reason why this can’t go on. You really don’t owe her anything. You do owe your sister to not “screw over” her friend. So whatever you choose, be upfront, and don’t force the issue if it’s not there.

You don’t take into account that if anything physical progresses with this girl, she will likely get the wrong impression and now you have found yourself in a mess. Girls look at things this way. If you invite her out to hang with you and your friends (and you’ve been on a few dates) she will assume you like her and like spending time with her. Yes you were trying to do a “classy booty call” but she doesn’t know that. If you truly don’t like a girl and just want to satisfy your sex drive, find someone with no strings attached, not someone that your sister is friends with and you will undoubtedly see again.

Good thoughts all around. Because I didn’t want to hurt the feelings of my sister’s friend, I took Karen’s advice to heart and planned to end up. I stopped the texting and booty call attempts. Then I was out for my sister’s birthday and of course this girl is there! Looming social awkwardness had arrived. Unfortunately timing wise, it hadn’t been that long since I stopped texting, so this girl seemed to think we were something more than friends as she was being quite affectionate while drunk. My sister actually pulled me aside to ask if any new developments had happened and I told her nothing had happened and nothing was going to. She thanked me for being a gentleman about it and I took that as my cue to give her the best birthday present ever: not taking advantage of her friend. So I paid my tab and left soon after. Hopefully, I won’t run into her until next year’s birthday.

Hello Vegas | Hello Lap Dance?

The Situation:

I am going to a bachelor party in Vegas this weekend and I just got an email from the organizer that we are getting a stripper to come to our suite one night. I figured it was best to tell my girlfriend and she was basically cool with it. It’s not like I go see strippers regularly—it is a bachelor party, a once-in-a-while type of thing. But then she says that while it’s OK if I see the stripper, I can’t get a lap dance. I explained that strippers in that situation might kind of give everyone a little lap dance, you know, dance around you, let you put a dollar in her thong or whatever, but she said that was an absolute no-no. Sorry, I am not going to push a stripper away at a bachelor party if she is giving everyone dances. I understand that your GF does not want this to be a regular thing or anything like that, but I don’t see anything wrong with every once in a while at a bachelor party seeing a stripper and getting a dance. Strippers kind of expect it and it’s not fun to be the guy standing in the corner with his hands in pockets because his girlfriend says “no dances!”

Am I being a horndog or is she being too controlling? Jordan and Karen, what’s the move?

The question of whether you can see a stripper while you have a girlfriend debate has been around since girls realized we will pay them to take their clothes off in front of us. And if you are in the same boat as me, it probably feels like there is another wedding and the obligatory bachelor party around every corner. Since this is probably not the last bachelor party with someone named “ecstasy” on the guest list, it’s important to resolve this issue with your GF now so that you don’t have the same fight every time the best man decides that the husband to be needs to see some boobs.

First, I want to commend you on the first step you took. You were honest. It’s never good to lie about this type of thing and with digital cameras, facebook and old fashioned gossip – she probably would have found out anyway.

So, to dance or not to dance? To me, it’s important to feel like “one of the guys.” No one wants to be in a situation where everyone else can participate but you can’t. You should explain there will be plenty of guys there who have girlfriends/wives and this is just an infrequent thing that guys do at bachelor parties. Explain that you will do your best to not get involved and that at most it will be a few seconds of a girl sitting on your lap. Reassure her that strippers and stripclubs are not two of your favorite past times, and that the whole thing will only take a matter of seconds.

Then go on about how you are respectful of her and that this is no different. This is merely a few seconds of a nasty stripper (emphasize how disgusted strippers make you feel in general) sitting on your lap. Also… it is not guaranteed that she will sit on your lap. Though discounts abound in this economy, one of the safest bets in Vegas is still that strippers will make you pay to play. And if that is the case, you promise her your money will stay in your pocket where you can use it to buy her presents – not in a stripper’s thong. So, maybe the worrying is for nothing, and it won’t even be an issue!

I don’t think she is being too controlling or that you are a horndog. She is being your girlfriend and you are being a guy at a bachelor party. With that said, you were upfront and honest about what’s going to happen and managed her expectations. Leave it at that. Go to the bachelor party and if the stripper gives you a lap dance, she gives you a lap dance. You come home and you don’t bring it up. Should your GF ask specifically if you got one, downplay it. You aren’t lying to her, you are making it less of a big deal. Girls will be girls. If Jordan explained the same Vegas situation to me, I would react the way she did, however, I would know that it would happen anyways (and I’m sure she does too). We bring it up to make our feelings known and to instill a little guilt in you when it happens 😉

Jordan’s Response to Karen:
I think what Karen said was dead-on. A girlfriend has to express her concerns when another woman will be that close to her man. We both felt that the most important thing was your honesty. I never thought about the guilt angle, but we men must always remember how tricky a woman can be, unless of course the woman happens to be a stripper and then I guess any interaction will be pretty straightforward!

Karen’s Response to Jordan:
I agree with most of what you said. You want to be one of the guys and this is what guys do at a bachelor party with strippers. I get it. That said, no need to go into details about only a few seconds of her sitting on my lap, strippers are gross, etc. It’s not going to make it better. I am smart enough to know that strippers are only gross when they are gross. If a hot naked women is dancing on you, it’s not gross. You probably think it’s awesome. Give your girlfriends some credit! Downplay the entire situation and her reaction will most likely be far less severe. The more ideas and thoughts you put in her head, the worse its going to be for you.
The Outcome:
Thanks for the advice guys! I tried to follow both Jordan’s approach of saying strippers are gross and Karen’s advice of downplaying the whole thing without spouting BS about how hot naked girls are icky. I basically tried to say that strippers are funny and not really sexual, that it will only take a few seconds and that she should just let it go because it wasn’t a big deal. When I called her out on just trying to make me feel guilty, she laughed because she knew I nailed her. So thanks for that one Karen! The stripper thing played out exactly how I thought it would. There were actually two strippers, one gross, one not gross at all. We all sat in a circle and they kind of gave us all dances, focusing mostly on the bachelor. When I got home, my GF asked if I got a dance, I said yes and that it was no big deal, and then she just dropped it. So it did seem that she really was just trying to make her feelings known and make me feel a little guilty (which totally worked by the way) and wasn’t really hell bent on making sure I didn’t get a dance. In the end, it turned out to be no big deal, so I am glad neither of us took a really rigid position to start with (I demand a dance! Never!) so that it did not turn into an unnecessary fight.