Dear Breathers: I'm gay, live with my parents, and never had a real relationship. How do I start dating?

The Morning Breath
Claudia Oshry @girlwithnojob and Jackie @jackieoproblems

Jackie and Claudia Oshry might be jobless, but they’re definitely not lacking insight. On their show The Morning Breath, the sisters will be doling out sage advice on anything their fans want to talk about: boyfriends, girlfriends, roommates, mom, dad, friends, or even dogs.

Do you have a problem only Jackie and Olivia Oshry can help solve? Email

Dear Breathers: My roommate I’ve lived with forever wants to and is planning on moving in with her boyfriend that she’s only been dating for 3 or 4 months. They’re signing a lease for a place on Wednesday and I don’t know how to talk to her about the fact that maybe she should wait without sounding like a brat that I’m just annoyed she’s leaving me. She’s my best friend but she’s very defensive and I know if I bring it up it will just cause a huge argument and a lot of animosity. I don’t know what to do. From, SOS

Dear SOS: If she weren’t your roommate, say she lived with someone else or another friend was moving in with a guy after three or four months, how would you handle it?

You should probably cover your bases and say something just in case the relationship goes awry. Maybe say something like, ‘Are you sure this is something that you really want to do?’ Just so it looks like you really care (even though you probably don’t).

But, when having this conversation, it’s important to make it all about her. Say something along the lines of ‘I have another roommate lined up so it’s not about that, it’s more about my general concern for you.’ If you have to lie a little bit, do it. Make sure to come across with an attitude that reads as ‘I’m not worried about me, I’m worried about you.’

Dear Breathers, I recently moved back in with my parents and we are opening up a totally awesome new restaurant. This has been kind of a chance of a lifetime for me, I’m a graphic designer and I’ve been given a large amount of control with the design of the place. I’m 24, I’ve never really dated anyone before, I recently got out of a super taxing “are we or aren’t we” type of relationship that lasted 3 years. Also it was long distance, like how much worse can it get? I live at my parents place about 45 minutes from a great city, there literally isn’t anyone around my town my age, and I’m also gay so I have to go into the city whenever I want to meet a guy. I don’t plan on living here for longer than 2 years but I really would like to not be such a newb with dating. I’ve been going back and forth about trying to find someone to date, if it’s worth the 45 minute drive and me still living with my parents. I’m not going to be living her forever but I also don’t want to be in a shitty mood because of how isolated I feel for the next years. I don’t know if you guys will be able to help, just want to hear what you guys have to say. From, Jan

Dear Jan: Go into the city and go on dates! 45 minutes is not that long, take an Uber, have a drink, and fall asleep in the back of the car. Do your business and get a date — you can do both! Sisters can have it all!

Also, definitely get on Tinder. Get on a dating app to set up dates so that when you go into the city you’re going in for a purpose and not just hoping to meet someone. Also, the internet is amazing, you just might find someone in your town, or even in a neighboring town.

Maybe even consider moving into the city and commuting to your job if you’re feeling too isolated. But always remember that it’s just a job and you need to get ass.

Dear Breathers, Six months ago I innocently came across the knowledge that my boyfriend of 4 years has a custom made engagement ring designed and ready to go for me at the local jewelry store. I swear it was an accident. Thanks, mom. It’s a small store so instead of financing it, he’s going to make payments until it’s paid off and he can take it home. I know it’s only been 6 months but I’m getting extremely impatient and I wish I didn’t know because now every time he spends money I get secretly annoyed and wish it was going towards my ring. I’m also contemplating offering to pay for it myself, which I know is totally crazy. So please help me before I get drunk, spill the tea, and ruin what’s left of the surprise. How does a girl keep a secret like this for so long? Should I come clean? From, Almost Engaged

DO NOT COME CLEAN! SHUT YOUR MOUTH, STOP EATING SO HE DOESN’T HAVE TO PAY FOR YOUR MEALS AND LET HIM PAY IT OFF. But seriously, in the next year be so frugal, pay for everything yourself, just make it really easy for him to pay off the ring.

Look at the fact that you know as a blessing because you can be prepared for whenever the proposal does happen. You can always have a manicure ready to go — and that’s not a luxury many have.

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