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Ask Kelly: How Do I Put Myself Back Out There After a Pandemic Breakup?

Also: Should you break up with someone who doesn’t support a major lifestyle change? Plus, how to decide whether you’re wasting your time in a long distance relationship.
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Hello and welcome to the second installment of Ask Kelly! I was absolutely over the moon about the response to last month’s column, and I’m so excited to dive right into this one. If you missed it, the topics were: how to choose and respond to prompts for your online dating profile, how to know if you should marry someone, and how to help a friend in a toxic relationship. If you want to ask me a question, please do!! I wish I could answer each question immediately, but please know that I read every single one and hope to eventually address them all in some way, shape, or form. Let’s jump in!


Hi Kelly! Thanks for starting this series, I'm really looking forward to it. Here’s the story: I'm trying to learn how to date again, after breaking up with my college sweetheart during quarantine. While there were good things about that relationship, I felt like I outgrew him in many ways. It was hard to end something that looked good on the outside, but I knew I deserved to be treated better. The heartbreak of the breakup was compounded by a lot of other personal losses, some related to COVID.

Even though I know myself so much better now, I'm so intimidated by dating nowadays. I've tried some dating apps, but I'm nervous about dating etiquette. I also have concerns about meeting in person, given all of the COVID restrictions. Also, to be honest, I don't want to waste time dating men who don't meet my non-negotiables (kindness, emotional maturity, sense of humor, and ambition). Finally, after dealing with some race-related issues in my previous relationship, I'm looking for someone who celebrates me in the fullness of my identity, including in front of their family.

When you put yourself back out there after your relationship ended, did you date casually? Or were you intentional about only pursuing serious relationships? How quickly did you start talking about serious stuff, such as career ambitions, formative life experiences, etc.? And finally, I don't rush physical intimacy with new people. How do I respectfully convey those boundaries to someone as we begin dating? - Intimidated by Dating

Dear Intimidated,

I’m so sorry you experienced a pandemic breakup. I feel like those of us who were navigating heartbreak while in lockdown are forever in a special club–one we never asked to be a part of, but we can lean on each other because of the incredibly unusual circumstances. Breaking up is hard; breaking up while you are essentially locked inside, alone with all your thoughts and feelings is harder. You also went through other personal losses that made the breakup worse–I’m so sorry. The last two years have been rough.

I’m proud of you for getting back out there and trying to date again, even while you’re intimidated by it. College is such an easy place to date–full of like-minded people all around the same age!–and dating afterwards feels like an absolute zoo in comparison, even without the pandemic thrown in the ring. I love the way you’re approaching this, and I like the word “cautious” instead of “intimidated” here. I don’t actually sense a lot of fear in what you’ve written, just a thoughtful, careful approach during an absolutely insane time in the world. There’s nothing wrong with wanting to be prepared for something you have limited experience with, feeling a little anxious about your first time back out there, and not wanting to waste your time. All of that is totally normal, so take a breath, and know that there are so many people feeling exactly the same.

I applaud you for your list of non-negotiables: kindness, emotional maturity, sense of humor, and ambition. I encourage you to think of these particular things not as “deal-breakers,” but rather, as desired traits that your ideal partner would have that you’re actively looking for. Unfortunately, these things can take a little longer to feel out in a person and may not be immediately obvious on an online dating profile. Think of your real, actual deal-breakers as a separate category of things that are more immediately identifiable and decide what those are–for example, mine are smoking, using drugs, being an “active” member of any organized religion, and voting for Trump in 2020. Everyone needs a list of 3-5 tangible things to look out for that mean a relationship would be dead in the water, and they’re helpful to keep in mind as you’re meeting new people.

I took a long time (more than a year and a half) to be ready to date again after my last relationship ended. I’ve never been one to date “casually”, meaning, I’ve pretty much always dated with the intention of finding a forever person. But that doesn’t mean I haven’t gone on multiple dates in one week with different people; I definitely have! If you’re a serial monogamist (guilty), you may have to train yourself to be willing to entertain dating multiple people at once.

I think the key is in understanding that dating in the early stages shouldn’t be so serious. If you’re in the right headspace, dating can actually be fun! I don’t even usually call a “first date” a date at all. It’s more of a vibe check. A first date is just an opportunity to meet someone you don’t know and find out if you enjoy talking and hanging out with them. That’s it. So much of the heaviness of dating comes from taking the initial stages too seriously and putting pressure on a particular outcome. I’ve always been a fan of grabbing coffee, taking a walk around the neighborhood, or getting a drink with a pre-determined ending time as a first date, because there’s nothing worse than spending two hours and $50+ dollars with someone who doesn’t pass the vibe check.

You expressed some concerns about dating with COVID restrictions, and I had the exact same feelings. Although they have started to lift in most places in the U.S., you can still take precautions. Go on dates with vaccinated people only (which you can now list right on your Hinge profile), and suggest ideas for dates you can do outdoors. Or hell, suggest a FaceTime as your first date; it really isn’t as bad as you might think. The “first date” I had with my partner was technically a 30-minute phone call: he answered the phone by saying “Kelly!!!” and I liked him immediately. Anyone who doesn’t get it or isn’t willing to try is probably not the one for you.

You want someone who celebrates you in the fullness of your identity (as you absolutely should, and I’m sorry this hasn’t always been the case). Transparently, I am a white woman who has dated mostly white and white-passing men, so I have limitations for any informed advice here. If you feel comfortable, I would suggest having a conversation about race fairly soon after meeting someone you’re interested in, and see how they react. Have they ever been in a relationship with a person of color before? How do they speak about their exes? Do they default to crutch phrases like “I don’t see color” that imply they were living under a rock in 2020? I would also like to shoutout Brandon Kyle Goodman, who posts pretty often about their interracial relationship on Instagram. I have learned so much from them on this topic – how race is present in their marriage, and how their husband makes them feel seen.

Speaking of the weightier topics, a mistake I used to make was either talking about more serious things like career ambitions, children, and formative life experiences either way too early or far too late. Imagine my surprise when an ex-boyfriend of mine, five months into our relationship, suddenly sprung on me that he had been in rehab for alcohol abuse about a year before we met. That’s not something he needed to tell me right away (and would definitely have been misplaced on a first date), but once it was clear we liked each other and were heading towards a relationship, that’s something I considered a lie of omission. His parents ended up letting it slip while we were all at a wedding because he was busy getting shitfaced, and I was mortified. Once you’re mutually interested, maybe after a few weeks of lighter fare, shift the conversation to some of the weightier topics. It will either drive you in different directions, or solidify your compatibility.

Not rushing into physical intimacy is–and I cannot stress this enough–100% fine. Respect to every person out there and whatever their pace is, but I’ve personally never been in a situation where in hindsight I thought “Wow, I wish we would have had sex earlier!”. I once told an ex on our second date that when I’m getting to know someone, I have a sort of invisible “bubble” around me, and I would gradually let him inside the bubble as I got comfortable. Weird visual, agreed, but he understood the analogy immediately and let me set the pace. In my current relationship, being long distance was actually a great thing for us in the beginning. Every time we would venture into conversation that was a little past my intimacy boundary, I’d hit him with an “Access Denied”. That was my cheeky way of telling him I wasn’t ready (I like to deflect with humor), and he got it. Being long distance and talking mostly via text and marathon Zoom dates with virtually zero distractions meant we got to know each other so much faster than usual. So by the time we were together in person again, sparks flew, and my boundaries disappeared on their own.

Good luck(!!), and remember not to take early-stage dating too seriously. You’ve got this, and don’t forget that every first date you go on has the potential to be your last.

x Kelly


I've been dating my boyfriend for one and a half years now. We just moved in together four months ago. I recently went through a big change and quit drinking alcohol and really started to take my life back, and I feel so wonderful and empowered. He has become so resistant to my healing, stating multiple times that "these past two months have been hell" and "I just want to go back to the way we used to be." We started couples therapy and I also see an individual therapist and spiritual empowerment coach, but I feel like I'm going to have to break up with him because he doesn't understand my healing and is almost cruel about my new process/journey. I really feel like I'm not that different, just happier, more aware of my needs and not drunk multiple nights a week. Any advice would be welcome! - Jess

Dear Jess,

First of all, it takes incredible strength to make major lifestyle changes like the one you are embarking on. Even though we don’t actually know each other, I am so, so proud of you, and I hope you feel the same way about yourself. I typically feel compelled to write extremely long-winded answers that help the inquirer reach their own conclusions or look at something in a different way, but I’m going to keep this one short.

Years ago, in one of my past relationships, I had an ex who would get blackout drunk several times a month. I asked him to consider therapy and work on it, and he said no because he thought it made him weak. I asked him to try drinking less, and he basically laughed at me. The amount of times I sat there flinching while he slurred insults and accusations at me is, in retrospect, appalling. If this person had decided to get sober and work on himself, I would have cried tears of joy. Your partner should encourage you to be the best version of yourself. In these cases, hindsight is often 20/20. Anyone who doesn’t support your desire to work on yourself and heal doesn’t deserve to be in your life. Follow your instincts–leave him. And don’t look back.

x Kelly


Dear Kelly,

My boyfriend and I have been together for four months, are cross-country / long-distance and feel like we’ve finally found our person. I’m 33, he’s 28, and we are committed to being in a long-term relationship. He’s been the one to initiate Big Talks (exclusivity, future plans, kids, etc.) and I feel so fortunate to have found him. Being with someone so kind and caring has been a big change from my years of dating aloof dudes who don’t know what they want.

My issue? I really don’t want to be long-distance. He’s currently living on the West Coast while I’m back east in the town he grew up in. He moved there (a year before we met) after 16 years at home so he could “have an adventure.” We’ve talked about it at length, and decided that he will move back here with me at the end of the year to move in together.

While I’m thrilled to have found someone to spend my life with, I feel like I’m making an incredible sacrifice for this relationship. I am essentially waiting for him to be done with this adventure phase, which is super important to him. Being a few years older, that time in my life has come and gone. I spent nearly a decade between New York City and California before settling down in a place that truly feels like home.

When I asked if he could come a little sooner, he said he feels like this is the last time in his life that he’ll be living alone near one of his best friends and wants to savor it a little longer before we get married and have kids. I’m anxiously attached (clearly), he’s secure, and he’s incredibly confident we’re going to make it work. He set up a communication plan for us, and we have the rest of the year planned with visits to see each other regularly.

But these weeks apart suck. I’m constantly missing him, despite having tons of friends, active hobbies that keep me busy, and a rewarding job. I feel like I’m taking years off my life being in this state of longing, and it’s exhausting. I know that nothing is guaranteed, and I’m also worried this might not work out despite all the work we’ve put into it…and then what?

What do you think? Any advice? I know you’re dealing with long-distance as well and would love to hear how you’re handling it. – Waiting

Dear Waiting,

Ooooooh how I wish this column was a podcast!! Your situation has a lot of parallels to my relationship with my partner, Paul. As I started writing a response, I read your question to him, and we debated it for over an hour. I would have loved for you to just listen to how it went, but I’ll do my best to organize our thoughts in written form.

You sound a lot like Paul late last year: anxiously-attached, waiting for your person to move across the country back to where they’re from, five years older than your partner, and having a rough time with even two weeks apart. While we were still long distance, he used to talk a lot about how hard it was for him in-between our visits until I moved to Minnesota. Without going into too much detail, Paul’s childhood led to his anxious attachment style, which he’s worked on in therapy. I can’t imagine what being long distance would have been like for both of us without the work he’s put in. While I obviously missed him while we were away, I never had those feelings of constant longing. I had a secure, loving, attentive relationship with my parents as a child, and plenty to do while I was in busy season at work and getting ready to move across the country. I tried to support him the best I could, but it was so clear to me there was only so much I could do to make him feel better (besides moving even sooner). Paul took ownership over his anxious attachment and called himself out a lot.

When I was in my mid to late 20s, I hadn’t finished my adventure on the West Coast yet. I, like you, spent a decade in a big city, and decided in 2021 after 10 years in Los Angeles that I was ready to settle down in my probably forever city. It sounds like your partner hasn’t had nearly the amount of time away from home that you and I had, which helps you grow and gain new experiences and perspectives. Really try to put yourself in his shoes and remember what that time in your life was like, and how it shaped you.

For me, the hardest part about moving that I’m still wrapping my brain around is not being able to drive over to my best friend’s house for a night of TV on the couch. Friendships are important, and I don’t blame your partner for wanting to savor that closeness a little bit longer before you get him forever. You didn’t mention this specifically, but I can’t help but wonder if feeling like you’re starting to run out of time to have kids naturally is influencing your feelings. I’ve mentioned this before in a different answer, but I would consider getting your fertility tested if you have the means. It may help you a lot with the anxiety you’re feeling about this time before you and your partner really “start your life” together.

I also want to encourage you to explore your anxious attachment style, and really dive into why you feel the things you feel. If you don’t already see a therapist, I highly recommend finding one. It sounds like you have a lot going on outside of your relationship, which is obviously healthy, and I want to offer an extremely gentle reminder that you’ve only been dating for four months. So ask yourself why, despite a rewarding job, friends, and hobbies, you’ve tied so much of your happiness to your new partner. You stated in your question that waiting 10 months for him to pick up his life and move across the country feels like an incredible sacrifice – to you. You feel like you’ve found “the one”, but wonder if you’re wasting your time waiting around for him, even though he’s already agreed to move to you (I can’t even imagine how many long-distance couples fight over this for… years?), has already chosen a time frame for his move, and laid out a communication and travel plan for you to see each other regularly in the meantime.

Zoom out for a moment – it sounds to me like you’re having a hard time seeing all the things your partner is doing for the relationship. I asked Paul, and never once did he feel like waiting for me to move was wasting his time, even if he had had to wait longer for it to happen. Here’s a question for you: What is 10 months compared to the rest of your lives, if it’s what your partner, who is five years younger than you and in a different phase of his life, has asked for? You both seem to be on the same page that this relationship is forever, but do you actually believe that? Are you worried that in the interim before he moves back, he might meet someone else?

This brings me to a really important point that I discovered in my debate with Paul. I think there are two kinds of people: Those who believe life is short (so why wait to do exactly what you want), and those who believe that life is long (so what’s the hurry). You and Paul are very clearly “life is short” people. I don’t know what your experiences with hardship and loss have been, but Paul has seen a lot of shit. It’s easy for me to see why he’s a “life is short” person, and I empathize. Honestly, before ending my previous engagement and heading into the pandemic alone, I was definitely more of a “life is long” person. Just over two years ago, I developed debilitating anxiety for the first time and entered the hardest period of my life, by myself. These experiences (and others) transformed me into more of a “life is short” person. I feel so lucky to be where I am in life now. This new outlook made it much easier to find common ground with Paul, and I moved across the country at a time we both found acceptable–a month before my lease in LA was up. I think your partner is probably a “life is long” person, and it would be worth it for you to ask and see which he identifies with and why. And if you find out that you are different in this way, how might that affect your relationship in the future?

Digging a little deeper, I encourage you to think of your situation less in terms of sacrifice, and more about compromise. It doesn’t feel healthy or sustainable for either of you to frame finally being together as a sacrifice that either of you are making. I moved across the country this year (for many reasons–one of them was to be with my partner) and I don’t see any sacrifice in it at all. I moved because it was my choice; one I’ve been thinking about for years. That being said, I moved a little sooner than expected because it was a compromise with my partner, who was having a harder time with the distance than I was. I asked Paul what specific advice he had for you, and here’s what he said:

"I’m very familiar with that deep panicky feeling that you might be getting while you are away from your partner. But if this person is ‘the one’, you must choose to believe that those panicky feelings are not actually based in reality. It is a choice; a sort of cognitive override. And the more you do it, the easier it becomes. It reminds me of a silly old saying: ‘Whether you think you can, or you think you can’t, you’re right.’ It’s the notion of a self-fulfilling prophecy.

As hard as this can be, if you want it to work, you’re going to have to make the choice to walk the path that leads to success. If you really think you’ve found the one, I can’t think of anything more motivating to look deep within yourself in an effort to conquer the dark places within you that these feelings spring up from. Therapy can be huge in this.

Of course, looking inward is extremely difficult and I still struggle with it. Those anxiety-inducing, impatient, panicky feelings might last for years. But sometimes they will be eradicated. For example, when Kelly and I were still long distance, I often wondered if she would be more likely to stumble across “Prince Charming” in LA, and I felt our relationship was less secure due to distance. This unfair idea that somehow not being in close proximity to one another made her more likely to stray, while at times consumed a lot of my energy then, seems so absurd to me now. It sounds like you have a lot of good evidence to trust this guy! As did I with Kelly. I wouldn’t have fallen in love with her as quickly and deeply as I have if she wasn’t super trustworthy. Sometimes we just have to grit our teeth and put our hearts “at risk” for a time in order to realize that they are not, in fact, at risk at all.

The degree to which you succeed in altering your inner and outer reactivity to these feelings can and will serve as a proud indication of your progress in the world. It can snowball into a really remarkable series of self improvements. Isn’t that the reason we are all here?"

Good luck, and try to remember that finding your forever person is truly something worth waiting (a little longer) for.

x Kelly

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