Hi Sasha, I have a serious boyfriend who I live with and love. We have a tonne of fun together, get along great, have great sex, our families get along, he is wonderful, caring, supportive and has his shit together financially. I think there's a good possibility we could become engaged within the next year to two years.

I am a goofy and silly person by nature. In our relationship, I'm the "silly" one. While I don't mind this label whatsoever, I do sometimes wish my boyfriend was perhaps someone I could get sillier with sometimes. He does have a good sense of humour and we definitely find similar things funny but I don't find that we can get on a hilarious role of joke making and totally cracking each other up... ever. I have wonderful girlfriends and I do feel that this aspect of my personality is something that comes out when I'm with them. 

The other part of my story is that, I have a colleague at work, actually my boss, who really shares my sense of silliness and humour. We are often joking around and regularly are the only two people laughing at the same thing in a meeting. He's also a really good looking guy. I would be lying if I said I'd never experienced feelings towards him. It feels pretty great to share that with someone else. Sometimes I find myself wondering why I don't share this with my boyfriend and if that is a problem or not.

I love my boyfriend and so I feel guilty every time I have these feelings. I would never act on them, so that's not an issue. Not sure exactly what I am asking here. I guess it's how important do you think it is for partners to make each other laugh until they cry.... ? And if that is not happening, is that a bad thing?  J  


Okay, so you say you would never act on those feelings for your boss and while I believe you, it doesn’t mean that those feelings don’t exist. Right? Right. I mean, they are there, there’s no denying that, but now it’s time to figure out why you’re having them. 

First off, I don’t think any of this means you’re some cheating, scheming asshole. I think what’s going on with you here though is what goes on with many people when they realize that their future as a single person could be coming to an end soon. They freak the f-ck out. 

I won’t front. The idea of a lifelong commitment is a total trip, especially if you’re someone like me who gets nervous signing up for a free ten day yoga pass. So. Much. Pressure. But here’s the deal J, you’re totally getting ahead of yourself because no one’s even talking marriage at this point, so before you start weirdly projecting feelings towards your boss – which is what I really think is going on here - you need to figure out what’s going on in your current relationship. Because if you don’t, you could end up f-cking the dog and doing some sh-t you really regret.    

So guess what? I don’t buy that the only reason you’re having doubts is because your boyfriend doesn’t embody the spirit of Richard Pryor. So what is it? 

Is it that you don’t feel the spark anymore? You’re not attracted to him anymore? That he’s really actually a total snooze? Let me put it this way: is this a situation whereby you have all the basic comforts in the relationship, but you just, well, want more? Or or or are you just trying to find something wrong with this perfectly loving relationship because you have a tendency to self-sabotage?

The good news is that it’s one of these two suppositions; the bad news is that you've gotta figure it out. 

Thanks for writing in and keep your questions coming to [email protected].

(Lainey: attached – these new shots of Emily Blunt and John Krasinski because in my imagination about how their relationship works, I feel like they make each other laugh a lot.)