5 Awkward Relationship Questions Every New Couple Should Ask

Couple kissing

How to ask awkward relationship questions – you know, without terrifying him.

The stage between “dating” and “exclusive” is the most interesting of any relationship – but it’s also the most intimidating. On the one hand, you know each other well enough to feel comfortable, but not too comfortable (you still sneak away to brush your teeth and race back to bed like you woke up that way).

On the other hand, it’s make-or-break time: Is there a deal breaker looming under the surface of your beau’s personality you’ve yet to uncover? Below are 5 icky-but-necessary chats you should have as you transition from “maybe” to “official,” and how to handle your relationship questions without being a total buzzkill:

1. The money talk
Money’s one of the top points of contention between couples, so it’s an area that should be discussed thoroughly. It’s not just about where he stands financially now, but where he hopes to stand in the future (and whether his words match his everyday spending habits). Once you decide to commit, this chat should happen around the same time.

“It’s important to get an idea about their thoughts and views on finances,” says relationship expert Kimberly Moffit. “Is saving money important to them, or are they okay with living paycheque to paycheque?” Most importantly, do his values mesh well with your own? Don’t ignore a sketchy history or irresponsible spending – as a couple, this history will become yours too.

2. The family talk
Some couples take meeting each other’s families too lightly. Err on the side of caution, especially if you’re thinking about bringing your sig-o to a family event. Not only do fams get attached, but if you haven’t talked enough about your families beforehand, a bad first impression is likely to ensue. (For example, bringing a bottle of wine to his dad’s house – who’s a recovering alcoholic.)

“When a guy wants to be serious about the relationship, he’ll automatically introduce you to his parents and friends,” says relationship expert April Masini. “Let him take the lead on this one – for every friend he introduces you to, return the favor – and don’t introduce him to your parents until he’s introduced you to his.”

3. The relationship history talk
At some point, you’ll want to know what each other’s pasts involved – otherwise, you could trigger a bad turn in your relationship without even knowing it. For example, if all of his relationships ended because he felt smothered, and you innocently make him feel that way again, get ready to repair a boyfriend-shaped hole in your door.

“Don’t give him details about past relationships if they’re not solicited,” says Dr. Elizabeth Lombardo, Ph.D., author of “Better Than Perfect: 7 Strategies to Crush Your Inner Critic and Create a Life You Love.” Instead of getting specific, ask general relationship questions or share mistakes you’ve made and what you’ve learned from them. It’ll help you both open up about what you do (and more importantly, don’t) want reruns of in your love life.

4. The gifting talk
Special occasions are the ultimate test to find out if you’re on the same page. If you don’t have this talk, there’s a good chance you’re going to get him a designer watch and he’s going to get you a t-shirt (in a color you never wear). Don’t assume you’re on the same page – otherwise, one of you will definitely end up disappointed. “Establish whether or not you’ll be making plans to spend the holiday together so no one’s left in the cold,” says Justin McLeod, Founder and CEO of Hinge.

Keep gifting casual by making a game of it: Set a spending limit, choose a gift theme based on each other’s interests and see what the other comes up with. Be thoughtful, but not creepy. The longer you’re together, gradually amp things up in the sentimental department.

5. The exclusivity talk
The “seal the deal” talk is the grand poobah of awkward relationship questions. Done well, this talk helps clear the air on where you both stand with your relationship (or lack thereof). Done incorrectly, many a woman have been prematurely labelled a bunny boiler. “It often comes off as a threat, not a channel that opens communication,” says Masini. “If he wants monogamy, you’ll know because he’ll act like he wants monogamy.”

On average, this question pops up in the first three to six months of dating. The longer it goes, the less clear the expectations are and the more likely one of you will end up hurt. “If the uncommitted dating goes on any longer than this, you can bet your partner doesn’t plan to talk about it anytime soon,” says Moffit.

How do you handle awkward relationship questions with your guy?

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Image: Timothy Marsee

Krissy Brady

Krissy Brady is a women’s health + lifestyle writer who’s so out of shape, it’s like she has the innards of an 80-year-old. Instead of learning how to crochet, she decided to turn her emotional baggage into a writing career (genius, no?). You can follow her shenanigans on Twitter (you know, if you want).