Editor’s Note: It was the week of Thanksgiving and I was talking with Kate about my plans for the holiday, which entailed meeting my boyfriend’s parents for the first time. Kate’s husband, Joe, walked over to the table at that moment and when he learned about the topic at hand he turned toward me with a look of intrigue, excitement, and genuine care that only he could muster. We went on to discuss the topic of ~meeting the parents~ as a group, and it was a truly delightful chat.

My point in this anecdote? If you’ve got a question about relationships? Or, really, about life in general and all the nuances that come along with it? Joe’s your guy. He comes to each conversation with not only personal experience but also with the kind of empathy and vulnerability that assure you the answer you’re getting is not of the surface level variety. The guy cares and he gives good advice, which is why we tapped him to answer six relationship and dating questions that W&D readers submitted via Instagram on this, the Monday before Valentine’s Day. We hope you enjoy.

– Jackie, W&D Editorial Director

P.S. On this Wednesday’s episode of The Wit & Delight Podcast, Joe and Kate will answer more of your relationship questions, together, as the very good team that they make. The episode will be released at 12:00 a.m. CT on Wednesday—make sure you’ve subscribed ahead of time so you don’t miss it! Okay. On to Joe.

I’d love to hear your thoughts on compromise in a relationship. How do you do it effectively and how do you set boundaries when you can’t?

Compromise is a pivotal element in building the foundation of ANY relationship, but specifically with someone that might be your “significant other.” If you don’t find yourself compromising, you may be, in a way, dating yourself in the form of someone who shares each and every aspect of thought with you.

Ultimately, I think about compromising on a spectrum. Are there things that we should “let go”? Sure, and identifying them early is beneficial. Are there things that are worth “fighting for” by voicing an opinion that might differ from your partner’s? Absolutely. I’ve learned that while Kate and I have differing opinions on things, there are areas where I’ll speak up and there are areas that I might just let go—à la the constant evolution of “where should the couch go” or “what color should the cabinets be.”

Ultimately, I think about compromising on a spectrum. Are there things that we should “let go”? Sure, and identifying them early is beneficial. Are there things that are worth “fighting for” by voicing an opinion that might differ from your partner’s? Absolutely. 

Compromise is critical to the longevity of any relationship, and while the “meet in the middle” scenario might not be ideal, there is a massive benefit to having the dialogue so you can understand why your partner might be so passionate about their position. 

What are your top suggestions for working through a disagreement with a partner?

I’ve found that the first step to becoming a good partner is (in my case) becoming okay with disagreement. Like any couple, Kate and I had our honeymoon period where I didn’t disagree with a word she said. But when it became clear that she valued my opinions on various topics, I started offering them at will, and the disagreements began happening, which to my absolute dismay didn’t ruin our relationship as I thought they may have.

Understanding the gravity and context of what the disagreement is based on is, in my experience, something to pay serious attention to. If the disagreement began with which wallpaper to hang in the bathroom and escalated to how one is raising their offspring to be a fair and accepting adult, there are things that need to be talked about more frequently so the escalation isn’t as rapid. This said, some of Kate and my best disagreements started with something seemingly trivial that guided us to a conversation that very much needed to happen. 

I’ve only had two sexual partners. Men I go on dates with now freak out when I tell them. Why?!

This might illustrate how things have changed since I was out on the dating scene. I understand that answering a question with a question isn’t always ideal, but is this something that’s coming up on the first date? (I ask this without judgment as Kate and I breached a myriad of deep topics on our first date.)

From my (uneducated and unqualified) perspective, if a guy is freaked out by the number of partners that you’ve had, he might not be the right fit for you. The only thing I might think of is that he could be looking for a “quick hookup,” as the kids are saying these days, and that your experience may somehow freak him out—which might be a good thing? The earlier you know he’s not right for you, the better.

What advice can you give on keeping my spirits up while dating, and actually enjoying the process? It can be exhausting and disheartening at times.

What we haven’t and likely won’t cover here is my “life before Kate”—which is for the best. I will tell you that I dated for YEARS before finding Kate. I had long relationships, short relationships, good relationships, and a few really bad relationships. In retrospect, I now have the self-awareness to admit that I despise spending time alone. Sundays were always the worst. I was so desperately terrified of being alone that at times, I got into relationships to simply have someone to spend some of the scarier times with.

The process of dating itself can certainly be exhausting, but I did learn a lot from it—about the women that I dated and about myself; mainly, what I was doing wrong. I was so immersed in ensuring women liked me that I would become what I thought they were looking for, and it was pretty terrible. Unknowingly, but thankfully, that behavior stopped with Kate when I was vulnerable and honest with her, and with myself, and the rest has been the best. Consider the process of dating as one of self-discovery and try to accept it for what it is—something that’s sometimes very hard and sometimes very fun, and that can teach you some of the best lessons if you let it.

What advice can you give on moving in with a partner? How can I make the process go smoothly for both of us?

Moving in certainly isn’t what Middle America had defined back in our parents’ dating years. Be ready to have your partner see you at your absolute worst. Having the occasional sleepover when dating is fine (as long as it’s okay with your parents?), but the gravity of moving in together does eliminate that alone time that you may have had previously, so I suggest keeping up with your hobbies, your passions, and your friends that may have predated the person you’ve moved in with. The expectation shouldn’t be that once you’re cohabitating, you mirror one another twenty-four hours a day, seven days a week, but that you can more easily cook together and that instead of selecting a place to hang, you have a place you both share.

Speaking on behalf of my gender, we’re (I’m) cool with you taking the reigns on all of the decor and general flow of the space, but it will go a long way if you let your partner keep that one relic that he might come with—a piece of funky artwork, an old overstuffed leather chair, or a kitschy coffee mug; give him something that makes him feel like he’s not simply moving into “your” place.    

What is the best communication practice to develop in a relationship?

Hopefully, you come in with honesty, but in the event that you might not, or that you lose it through the initial time of dating, honesty is the best policy.  Honesty reigns supreme, and I’ve found that even when I’m ashamed or embarrassed by something, honesty is more important than whether Kate approves of what I’m telling her.

Honesty reigns supreme, and I’ve found that even when I’m ashamed or embarrassed by something, honesty is more important than whether Kate approves of what I’m telling her.

The same goes for the time when your partner shares something that requires them to go out on a proverbial limb—if it makes you sad, or mad, or glad, or you’re indifferent, I find that positive affirmation and appreciation of their transparency is key. If your partner tells you something that took time to muster the confidence to say and your reaction does not meet the level of emotion exhibited, it’s not going to go well. Always, always think about what your partner might be feeling in response to the situation; context is imperative.