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Ask Kelly: I’ve Never Used An Online Dating App. Help!

Also: How to know if you should marry someone, and how to help a friend in a toxic relationship.
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Hello and WELCOME to my first shot at answering your incredible questions for Ask Kelly! I was humbled, blown away, and straight-up ecstatic about the response to my introductory post and first installment in this series, and my only regret is not being able to answer more of the amazing questions you sent in at once. While I’m certainly no expert (a therapist is always the best person to ask for advice on basically everything!!), I have a lot of experience with dating over the past 20 years, both the shout-it-from-the-rooftops and let-me-just-crawl-in-a-hole-and-stay-there kind. This column may not be for everyone–totally get it, not at all offended–but for those who want/need/enjoy it, I hope it’s everything you were looking for. Connecting with you all is one of my favorite things about my job and a major reason I remained sane while living by myself during the pandemic, and I can’t thank you enough for the heartwarming interest in this wacky idea. So without further ado, let’s jump in!


Hi Kelly! My long time boyfriend and I split up during lockdown, after deciding our priorities were simply different. I'm reentering the dating world in the middle of a pandemic, having never used a dating app - basically, I need help! After downloading Hinge and uploading pictures, I'm completely stuck at the "Profile Answers" section. The wide variety of prompt options has caused me to overanalyze how my answers to these seemingly trivial questions will come across. I'd like my personality (clever, humorous) to shine through, but I also want to be taken seriously without looking desperate. What types of questions have you found to be the most beneficial for this section and how do you strike the right balance? Thank you! - Needing Help With Hinge

Dear Needing Help With Hinge,

I’m so sorry you went through a breakup during basically the toughest time in modern history to go through such a thing. Having different priorities is something that I think the pandemic forced out into the open for many couples, and I applaud you for moving forward and re-entering the dating world, hopefully with some gained perspective.

It’s funny that you say you got stuck at the “profile answers” section of Hinge, because that has happened to me, too. Last summer I had been carefully thinking about my photos for at least a month before even downloading the app (for the fourth time…), but when it came time to answer three short prompts out of what seemed like a million possible choices, I put my phone in my pocket and took a few hours to really think it through. You’re right – the questions are trivial. It’s impossible to convey an entire personality in three short sentences, and it’s important to strike a balance between not taking yourself or dating apps too seriously, while also conveying that you’re serious about finding a partner. So, what’s a gal to do?

Here’s my advice:

  1. Choose one question that’s a simple conversation starter that virtually anyone could respond to. Make it easy and painless for someone to strike up a conversation with you – give them some low hanging fruit, if you will. I chose the question “The first drink is on me if”, and I answered with “you can guess how many books I’ve read so far this year.” A majority of men who “swiped right” on my profile went for this question, wagering a guess and offering a few comments about what they like to read, which I could talk about all day. This type of question is a good ice breaker that will communicate that you’re approachable, and it should ideally reveal something about your personality as well (I’m a book reader, obviously; it’s one of my major hobbies).

  2. A second question that’s good to answer is one that reveals a little something unique about who you are and what you’re looking for, without being too direct. I picked the prompt “Together we could”, and answered with “become the next Chip and Joanna Gaines???”. I had been binge-watching Fixer Upper and painting my apartment that summer, and it dawned on me that if I moved to Minnesota like I was planning on doing eventually, I could actually afford to flip houses if I found the right partner to do it with. I’ve always loved interior design, architecture, and DIY projects and saw the potential for something like that in my future, so I decided to go for it. Sure enough, this is the prompt my boyfriend responded to. As a real estate agent who was in the middle of flipping his second house, he knew this question was the perfect in to get a conversation going with me–and he was right. We immediately started talking about flipping houses, and pretty quickly asked for my number so he could send me pictures of a vintage spiral staircase he was installing (for those reading who don’t know: a vast majority of conversations started on dating apps live and die within the app and never actually make it to text). Our interest in each other was immediate, and I have this question to thank for helping me start a stimulating conversation with a stranger that virtually never stopped.

  3. A final question I think you should add is one that shows your sense of humor. Your dating profile is designed to attract someone to you, so have fun with it! It doesn’t have to be so serious and communicate a laundry list of things you’re looking for. Instead, your profile should exude an overall vibe and stay pretty light. I chose the prompt “We’ll probably get along if”, and I answered with “you remember to get me a side of ranch.” I am obsessed with ranch, on everything. It’s a little self deprecating, funny, and not at all serious. Sometimes dating is about making sure you’re in line with religion/politics/children/life goals, and sometimes it’s about simple things like ranch dressing and being able to poke fun at yourself.

And a few don’ts?

Don’t be too intense. I’ve seen a lot of profiles made by someone who has clearly been burned in the past, and it shows. Answers like “I’m looking for someone who is honest, trustworthy, and loyal–just be a good human” communicate that this person has likely been hurt and has walls up. This person isn’t ready to date yet, and would be a swipe-left from me.

Don’t try to fit too much into one answer. These prompts are meant to start a conversation, and that’s about it. It’s only three sentences, so don’t worry if you feel like you’re only scratching the surface. That’s how the app was designed, to get you off of it as quickly as possible and meet someone in person.

Don’t answer inaccurately. It’s tempting to answer a question in the way you think might be the most widely appealing, but if it isn’t accurate, they’ll find out eventually. If you prefer a more planned or researched approach (me), don’t say that you’re spontaneous. If you have flight anxiety and like to travel a few times a year (also me), don’t say you want to visit every continent before you turn 40. Just be you, even if the majority of people like something you don’t. The right person for you is out there, but you have to help them find you by being honest about your preferences, goals, likes, and dislikes.

Remember, these prompts are only meant to start a conversation, so don’t take them too seriously. Be confident and give people a hint of your clever personality. Save the rest for when you meet in person. Good luck!

x Kelly


Hi Kelly! I am going to ask you a question that only I can truly answer, but I want your advice. I'm currently living with a man I've been dating for two years and honestly, it's going great. He and I are really compatible and want the same things out of life for the most part. But a few things keep nagging me–our differences in being stoked about adventure and physical endeavors, excitement to have kids (I really want them!), and I've never had that head-over-heels-in-love-I-know-you're-my-person feeling for him. I'm turning 30 in a couple weeks and feeling the time pressure to either get engaged or move on. I'm worried that my desire for a family, fear of finding anyone better in a pandemic, the perfect love-story Disney princess narrative, and the logistics of separating our lives (I LOVE our apartment) is going to keep me from really evaluating what I want and need. How did you overcome those fears and expectations? How do you know if you should marry someone or not? - Fearful There Might Be Someone Better

Dear Fearful,

You’re absolutely right–this is a question only you can answer. There isn’t a magical formula that can tell you whether you should marry someone or not, just like there’s nobody but you who can decide what city to live in, what to do for work, or what your favorite food is. Every decision you make is yours. It’s kind of overwhelming. Unlike choosing what to get for dinner tonight, though, choosing a life partner is one of the most important decisions you’ll ever make. The next 60 years (we hope!) is equivalent to about 40,000 meals you could potentially eat with this person if you ate twice a day together for the rest of your lives. I know that’s a weird example, but isn’t it kind of mind boggling to think about? Your life partner will be your roommate, dinner date, travel companion, confidant, co-parent (to either humans or animals, if you choose that), and overall, your best friend. Sixty years is a long time with the wrong person. Unfortunately time travel hasn’t been invented yet, so there’s no way to temporarily head to the future and check out the ramifications of your decision making, so we have to do the best we can with the information we have available now when making life altering decisions like these. And I think you’ve already decided.

Perhaps this is going to be a bit of a hot take that follows, but let me tell you why I think you’ve already made your decision not to marry him. You described your current partner as “a man I’ve been dating for two years.” Not “my partner”, “my possibly forever person”, “my best friend”, etc. In contrast, you said you LOVE (in all caps!) your apartment that the two of you live in together. You say you’re compatible and you want the same things, which is capital I Important. But you’ve also admitted you’ve never felt that “I know you’re my person” feeling for him. You actually even listed out four (four!) reasons why this relationship probably isn’t going to end in marriage–and one of them is simply the logistics that would be involved with separating your lives and moving out, which I find to be very telling (and I’ve been there). One of the other reasons you listed, though, is the nail in the proverbial coffin for me: You said you’re afraid you won’t be able to find someone better during a pandemic. Well, the pandemic is sort of here to stay, and it sounds like you’re more afraid of being alone right now (trust me when I say I understand, it sucks) than potentially losing your current partner. Learning how to be fine on your own can be an invaluable lesson, and not wanting to be alone isn’t a reason to stay in a relationship (let alone get married!). I think fear is holding you back from actually acting on a decision you’ve already made.

Speaking for myself, after going through something very similar when I was 30 (and then heading into the pandemic on my own, ready or not), I adopted a pretty simple way of viewing major decisions in my life. It doesn’t apply to absolutely everything, but it’s a good way to zoom out and view an idea from a bigger-picture lens. The principle is this: It’s either a fuck yes, or it’s a no. I know a lot of people will read that and say, “But wait! It’s not that simple!”, and I hear you. But it can be. Turn the tables around for a moment and ask yourself: Would you want your future husband to be a little lukewarm on marrying you, or would you want him to say “fuck yes” to you?

I know entering your 30s is a major milestone, and a somewhat emotional rite of passage for many women, but don’t let the idea of leaving your 20s pressure you into making a decision for the wrong reasons. To hell with society and its views of where women should be and what we should be doing by a certain age! Letting go of that pressure was the best thing I ever did for myself. You’re 29 – you have plenty of time to start over with a new partner and have kids, if that’s what you want. Do not let the court of public opinion make you feel otherwise. If you’re anxious about being able to have kids that are biologically related to you someday (and have the means to do so), get your fertility tested, and see what you’re working with. I have friends who have frozen their eggs and felt an enormous weight lifted off their shoulders by releasing a bit of that time-pressure burden. And if your partner isn’t really on the same page as you on wanting kids and when, well, that’s another sign it isn’t right. Both my boyfriend and I have had to end relationships with ex-partners in the past (mine amicably, his horribly) because we weren’t on the same page about kids. I really can’t stress enough how important that is.

I know that making a life altering decision like this isn’t easy, and being on your own again is hard. When relationships end, people get hurt. It’s unavoidable. Maybe I’m totally wrong, and this relationship is actually right for you–only you know that. No matter what decision you make, make it knowing that you’ll never know if it was right, but you’re doing the best you can with the information you have. Be kind to yourself (and your partner) in the months ahead, and remember that fear is the mind killer.

x Kelly


Hi Kelly,

My friend has been dating her boyfriend for about four years now. He’s nice enough (and I don’t think there’s any abuse involved), but I wouldn’t say he’s great to her—he just isn’t very kind or respectful. Every time I meet up with her, our conversations are derailed by her complaints about him—to an even greater extent since the start of the pandemic. I really value this friendship, but I don’t feel I have any more empathy to give on the subject. I’ve suggested she speak to a therapist about this, and I’ve tried asking her leading questions about what she wants to do. Basically, what’s a way I can shift the conversation to a more positive space, or, more directly, what’s a kind and compassionate way to say, “girl, either break up with him or stop talking about it”? – Out of Empathy

Dear Out of Empathy,

Oof. This is a tough one. I’ve been your friend in this situation, and I wouldn’t have gotten through it without the truly staggering amount of empathy presented to me by my ride or die, Jessica Kane. She was right there listening to me for something like an entire year while I expressed doubt about my relationship, cried with frustration over the way I was being treated, and worked through the paralysis that prevented me from actually doing anything about it. For over six months we commuted to work together (about 45 minutes each way), and every day there were always two items on the agenda: listening to Taylor Swift, and talking about my problems.

I asked Jess what her experience was like as the one in your shoes, and here’s what she had to say:

Truthfully, Kelly and I haven’t spent much time reminiscing on this period of our friendship – it was tough for me and even tougher for her – so it feels a little funny writing about it, knowing she’s going to read it here! I can definitely relate to your current situation, and have such clear memories of engaging in conversations similar to the ones you’re alluding to. I distinctly remember the very first time Kelly confided in me. My spidey senses started firing off that this guy likely wasn’t worthy of my friend, but I listened and held as much space for her as she needed, because from my experiences, that’s what friends do. After a few months and many disheartening conversations, that space did get tougher to hold. It became an emotional balancing act of providing compassion, understanding my own biases, and realizing that, frankly, I couldn’t totally relate to her situation, and therefore giving her a little bit of grace.

One detail that’s worth mentioning: I knew Kelly well, so I could sense that she was aware of her own worth, and strong enough to leave…eventually. It made the many months more bearable, since I felt confident that it would happen and my friend was capable. I wanted her to feel supported so that when she did decide to leave, there was no external pressure or influence – she had total agency and ownership over her choices, and was therefore more confident in them. If you’re less optimistic about your friend’s conviction…I may not be able to help.

A useful exercise? I began asking less about the specifics of arguments, and more about the broader patterns or recurring behavior I witnessed. I very consciously posed them in a way that removed her personal investment in her own relationship: by asking, “if a loved one was experiencing an analogous situation, what would you tell them?” From my perspective, as she failed to rationalize the behavior for a friend or family member, she slowly but surely saw that there was only one way out.

So unless you’re ballsy enough to ask her “Is your current relationship better than being single?”, I’d suggest having faith that your friend will leave him on her own time. For now, while you may not have much, muster up as much empathy as you can. I promise she’ll thank you for it in the long run.

Here’s the truth: Deep down, your friend probably already knows what she’s going to do. She’s either decided she’ll have to leave the relationship at some point and is constantly trying it on like you might a pair of jeans that no longer fits, but they were once your favorite pair, so you keep trying them on and looking at yourself in the mirror and imagining if you’re really, actually going to finally give them up. Or, she’s decided that she’s going to stay in the relationship come hell or high water, and she’s trying on what that looks like in the forever sort of sense. She may be complaining constantly because she knows that she’ll be dealing with whatever she’s not happy with for the foreseeable future, but she can’t actually change his behavior, just like you can’t just straight up tell her to stop talking about it. If she stays with him, whether it will work out in the long run or not remains to be seen, and isn’t your problem. Your duty as her friend, if you value her and want to stay in the friendship, is just to listen.

I know your empathy is running thin, and I understand why. It’s hard being around toxicity, especially when it feels like she’s not working towards a solution. If you’ve suggested she speak to a therapist and that hasn’t worked, I encourage you to do a little research and see if you can help her there. She may be paralyzed by the idea of finding a therapist and needs someone to help her, but doesn’t know how to ask. When I was in her position and finding a therapist for the first time, I went with the one and only person recommended to me by a friend. It made a massive difference and meant that Jess wasn’t bearing the entire burden of my feelings, because that isn’t her job.

If you’ve reached your breaking point with this friend, gentle honesty is always a good policy. Instead of telling her that you’ve had enough and you’re out of patience, try changing the angle and speak from the heart. Tell your friend that it’s getting too hard to continually see her in such conflict within her relationship, because you care about her and want her to be happy, and that clearly isn’t the case. After that, if it’s affecting your own mental health, you can start distancing yourself from the friendship until something changes. If and when it’s over, be at her place with pizza and wine and remind her that she isn’t alone.

x Kelly

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