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Ask Kelly: Should I Be Hurt After the End of a Short Situationship?

Also: How to address a lack of experience with long-term relationships? And, would a "Dating 101" guide be useful?
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Dear everyone, I love the questions you’ve been submitting to this column. Keep it coming! :) If you missed last month’s column, read it here. My mom texted to say it was “the best one yet,” so there’s that I guess!

Hi Kelly! I’m recently divorced after nine years together. Not ready to start dating, but I always do my homework, and need some resources for when I am ready. Apps didn't exist when I dated in the past, so I'm completely out of the loop. Also, I’m 37 with no real dating experience – my two long term relationships started as friendships. So, I have a million basic questions: Is there a good central resource to reference? Which app(s) do I use, how do I choose pictures, what should the first date be, how do I screen people, etc. Literally every “Dating App 101” question :) Also, the big kicker: When did you feel ready again??? - Megan

Dear Megan,

I truly love this question, and it lands in my inbox so much that I’m toying with the idea of creating an “Online Dating 101” guide that goes over every topic you listed in depth, and more. There’s simply TOO MUCH to distill what I’ve learned in 10 years of online dating and the “secrets” to how it worked for me (and many of my friends) into a single answer. So here’s my question to you all: Would a manual of this kind be helpful??? Would you use it? Are there other online dating topics you would want a “guidebook” for? Come tell me here, TYSM.

While I wait to hear from you all about whether this dating manual (lol) would be of use, let me skim the surface of some of these questions. Megan, I’m proud of you for even being willing to think about trying online dating when you’re ready. I’ve heard a lot of pushback from people about using apps when they’ve never tried them before, but how will you know whether something will work for you if you don’t give it a try? That’s one of the best pieces of advice I can give for online dating. Try, try, try again. Keep trying. Don’t. Give. Up. The payoff of finding a partner is well worth the journey to get there.

Which apps should you use: Hinge (to find a long-term partner), Tinder (to find something casual), Bumble (to go on a lot of dates and get that out of the way). If the idea of something only app-based is unappealing to you, try or eHarmony.

How do you choose pictures: This is one of my favorite online dating topics, but my advice can be distilled into: “Come as you are.” I can’t stress this enough!! Make sure your photos are accurate based on what you look like today, and reflect who you are and what you like to do. Make your photo selection a representation of yourself as a whole person with a personality that jumps off the screen. Be proud to show yourself off! People are generally very attracted to positivity (aren’t you?). A genuine “I’m actually having a great time” smile goes a long way.

There’s a lot more to unpack here and reasons behind these recommendations, but include at least one full-length photo (head to toe) and one up-close shot where it’s absolutely 100% clear what you look like. It shouldn’t be an actual headshot (this isn’t LinkedIn lol), but when someone meets you in person, don’t surprise them! Include photos of you alone and with friends, and at least one of a hobby or activity you like–preferably something a little unusual. Never cut an ex out of a photo, no matter how good you look. Get rid of selfies; they distort your face and give off a certain vibe that could read as narcissistic. I have a LOT more to say here (this section is basically all about marketing, my area of expertise!) but if you only take one piece of advice from me today, smile in your main photo. With teeth. And have someone else take it (again… not a selfie).

What should the first date be: I like to avoid dinner if you can, unless you’ve screened your date on a phone call or FaceTime first. A drink is fine, but coffee is better. Remember that on a first date, the person you connected with on the little internet box might be totally different in real life than you were expecting. I showed up to a first date at a Starbucks and realized pretty quickly that the guy I had been chatting with for a few days was super weird and looked nothing like his photos–thankfully it was just a coffee date and I bailed out of there after 20 minutes of small talk! Never, ever go to someone’s house or apartment (or have them over to yours), and don’t have them pick you up, either. Get yourself there and back, and only meet in a public place. Always, always prioritize your safety over anything else. And always try to have a friend who knows where you’re going and when, who you can call after to debrief!

How do you screen people: This depends entirely on what you’re looking for! Always look for respectful discourse in the chats and listen to your gut if someone is giving you a weird vibe.

As for how and when I felt ready to date again after going through a big breakup (and then Year One of Covid…), that took time and working through the past in therapy. There was a natural slowing in our sessions that happened over the course of a few months. My therapist actually pointed it out to me first–that I seemed to be in a much better place than when we started our sessions together, and might be ready to start dating again. I held off for a long time because I wanted to make sure that I was in the right headspace to actually get into a relationship if I found the right person. I do think in some cases it makes sense just to throw yourself in the pool when you feel you’re not totally ready (a little push is sometimes a good thing!) but for me, I wanted to go into dating with a super positive, optimistic attitude, so I waited until I got there on my own.

I completely relate to you saying that you want to do your homework in this period before you’re ready to date again (more than you know, haha)–seek out some friends who have met their partners online or after a divorce, take them out for a drink, and ask them to tell you about their experiences. Online dating is extremely common these days, and leaning on friends who have been there before is essential! Hearing other people’s stories should make the whole process feel a little less intimidating. I promise it’s not as bad as you think, and expands your dating pool exponentially.

GOOD LUCK, and I hope that your first foray into the online dating world is mostly stress-free, and dare I say… fun?

x Kelly


Hi Kelly. I’m 30 years old and have never been in a romantic relationship. I’m very independent and quite comfortable being single, but as I get older I become more and more concerned that my lack of relationship experience will be a turnoff or red flag to potential partners. How should I address this or best answer questions from dates about my lack of relationship experience? – Old Maid

Dear Maid,

First of all, it hurts my heart to know that we’re living in a world where a 30-year old woman will willingly categorize herself as an “old maid.” I’m a few years older than you, and I still feel young as hell. We as a collective need to do everything we can to shatter the illusion that a woman’s worth is tied to her youth or relationship status. I looked up the origins of the term “old maid” online and learned that in addition to meaning an unmarried childless woman, it also means an unpopped kernel in a pot of popcorn. I like that! Maybe you just haven’t popped yet.

I chose your question to answer because I didn’t immediately know how I would respond, which intrigued me. I think discussing this with a therapist would be enormously helpful, and I’m curious as to what they would have to say. What follows will be an amalgamation of my thoughts over several weeks of thinking about this question and asking friends for their opinions.

I love that you’re independent and comfortable being single, so congratulations. Many people never get there, and I think it’s an incredibly healthy and important thing to accomplish. I wonder, though, what the reasons are that you’ve never been in a romantic relationship before. I think that’s what we need to answer first here, for you, before we can figure out what the best way to address this with a future potential partner will be. So follow me for a little bit while I ponder a few options:

Maybe you’ve never had a relationship before because you’ve been preoccupied with your career. Maybe you never really dated in high school and college (if you attended) because you were focused on your grades, and you dove head first into a demanding career that commands all your attention. Now, you’ve woken up at 30 realizing you’ve never been in a relationship before, but it sounds like you might want one now. I think honesty is maybe the best policy here. But if this is the reason, you have to commit to making time and space in your life for a partner if you find one. A potential partner might be worried that you won’t make time for them, and I think that’s a valid fear. Be willing to show someone exactly how you plan to make space for them in your life and how you’ll prioritize them with a demanding career.

Maybe you’re afraid of putting yourself out there. I’m shy! I get this. When I was dating, the idea of walking up to someone IRL and asking for their number gave me hives. I was always terrified of being immediately rejected or informed that his wife was actually in the bathroom, so I truly never met anyone in that way. It takes a mad amount of confidence and a “YOLO” attitude to not give a crap about being rejected to your face, and I seriously admire people–especially women–who are willing to put themselves out there like that. On the flip side, if you sit at home and read books all day (formerly guilty) you’ll never find a relationship, either. Unless you’re willing to try online dating, which is why I have so much experience with it! Online dating is an incredible way for shy people to find a relationship, and you can do a lot of it from the comfort of your couch. If you’ve never done it, I highly recommend giving it a shot. It can actually be enjoyable if you go into it with the right attitude.

Or maybe you’re just extremely picky when it comes to looking for a partner and love your life exactly how it is. Would I be wrong guessing that dating truly has never been a priority for you? I have a friend who didn’t have her first major relationship until she was in her mid-thirties. She was so happy on her own that dating wasn’t a priority to her, and she subsequently never found herself in a relationship before she went actively looking for one. That probably sounds like a “duh”, but most people don’t accidentally find themselves in relationships. You have to actively look for one–or be willing to say yes if/when approached by someone who is interested in you–and if you’ve never done that, it makes perfect sense that you’ve never been in a relationship before. If that’s the case, I’d recommend examining the reasons you’ve been so picky evaluating potential partners and really breaking them down one by one; finding a therapist could be super helpful in that process. Happiness in a relationship doesn’t really come from checking all the boxes off on a long list of things we *think* we want, it comes from really knowing ourselves and finding a compatible partner who we share a deep connection with, regardless of how many “boxes” they may or may not check off.

Whatever the reason, talking about this with others will be a little tricky. I personally wouldn’t lead with this information (but don’t hide it if your date directly asks). When you’re in the casual first stages of dating, let’s say the first few dates, I’d leave this topic off the table. Never having been in a relationship before doesn’t have to define you or hold you back in the dating world, as long as you’ve unpacked with yourself what the reason(s) are. Your dating history isn’t anyone else’s business unless you’re invested in someone and beginning to explore a relationship with them. I would hope that the right partner for you wouldn’t run away because they find out you’ve never been in a relationship before (and if they do run away, well, clearly they aren’t the right person for you). As long as you’re willing to talk about it openly with a potential partner once things get a little more serious and figure out with them how to address any issues that might arise from it, I think you’ll be just fine!

If someone directly asks you on a first or second date, here are two options to consider. You can choose to set a boundary, and say something like: “I’ve never been in a relationship before, but I’d love to save that topic for another date.” If you want to answer the question briefly, don’t make it seem like an accident–explain it like a choice you made deliberately. I’d rather hear: “I’ve never been in a relationship before, but I’m making it a priority now because I woke up one day and realized my career will never love me back and a relationship is something I now know I want” rather than: “You know, I’m not totally sure why I’ve never had a partner, I guess I just never really cared enough to figure it out until now.” Whatever it is that has held you back until now, be honest with yourself first, and that should steer you in the right direction.


x Kelly

Hey Kelly! I was seeing someone for about a month and a half, and it was one of the best, most exciting situationships I've had in a long time. He was very attentive at first - making lots of quality time for me (my love language), great text banter, even using phrases like "if we start dating I'd like to do this with you". About halfway through our time together, I noticed a shift in his behavior. It felt like I'd done something wrong or he was losing interest, but I had no idea what had changed. When I told him how I felt about him and asked him if he could see this turning into a relationship, he told me that he was still very hurt by his ex who had broken up with him two years prior and that he "needed time" to see if he was ready to start something with me. After a week of constant texting, he told me that he wasn't ready and then ghosted me when I attempted to respond to him. I'm still very hurt by the experience; I identify as demisexual so opening up to new people physically and emotionally is hard for me. I also feel as though I don't have a right to have all of these emotions about the experience or be so hurt by it since it was such a short time that we saw each other. Are all men like this? Any advice for moving on? –Emma

Dear Emma,

First of all, kudos for using the word “situationship” in your question! I love it. I’m so sorry you had a bad outcome with this person, and I think you already know this, but you didn’t do anything wrong.

The first few weeks of dating someone new are often really fun and exciting, but also very hard because it involves two people getting to know each other on so many different levels. Is there chemistry and attraction? Similar interests? Long-term compatibility? Good communication? Genuine excitement about the other person? So many could-be relationships don’t make it off the ground because one (or both) people come to realize that something isn’t working for them. It could be something major (like political differences or a serious personality clash) or something very minor (like a general feeling that something is missing). When you’re in the dating pool and someone chooses not to continue exploring a potential relationship with you, it doesn’t mean something is wrong with you, or that you did something wrong. It can simply mean it just wasn’t a “fit,” for whatever reason. Learning to be okay with (and even appreciate) that is something that just takes time. Trust me when I say I’ve been there.

There is a level of self-confidence necessary in what I’ve just said that I recognize is tougher than it sounds. When someone decides to call something off with you at any point in a situation or relationship, it sucks. Plain and simple. But in the bigger picture, it can actually be a good thing. You won’t be stuck dating someone who is only half in it as your own feelings keep developing. You’ll keep learning about yourself and have a better idea of what you want and need in a relationship. You’ll find that bouncing back from rejection gets a little easier every time you do it. When it’s your turn to reject someone, you’ll do it kindly and with compassion. You’ll realize that not being the right fit with someone isn’t the end of the world, and is actually pretty common for everyone. Your person is out there, and you shouldn’t have to settle for someone who isn’t as excited about you as you are about them. When I was 24, I dated someone for six months who broke up with me completely out of the blue. I’m embarrassed to admit I basically begged him, sobbing, to change his mind, and he said to me: “I’ve just told you that I’m not in love with you and you aren’t right for me. Why would you want me to stay?” I’ve never forgotten it. I think what he said was harsh, but not wrong. It took me years to understand it.

I’m so sorry for how awful you’re feeling. To answer your question directly, you have every right to feel your emotions as they come, and all the people you will date in the future are definitely not like this. What this person did wrong was ghosting you after you had been hanging out for over a month–that’s shitty. I hate that for you. I hate that there are people out there who think ghosting someone that far into getting to know each other is appropriate. It isn’t! It sounds to me like he’s a bad communicator, and that will probably follow him around to whomever he dates next. But calling off a situationship after about six weeks is actually okay to do. I know it hurts, but there’s a chance he either met someone else, or just didn’t see a future there. Whatever the reason, he absolutely owed you an honest conversation, and not having one robs you of getting the closure you need to move on.

Of course in a perfect world we wish that people would know almost immediately whether they want to be in a relationship with us or not, but that unfortunately isn’t reality. We have to allow ourselves, and our potential partners, time to get to know one another before making those decisions. It’s not what he did, it’s how he did it. Saying he isn’t sure he’s ready to start a relationship after he and his ex broke up two years ago is probably bullshit, whether he knows that or not. My guess is that the connection he had with his ex is stronger than the one he felt forming with you. And while that obviously sucks, it’s okay. There’s someone else better out there for you, and they’re worth putting yourself back out there for.

I hope this doesn’t sound cliché, but my best advice for moving on is: know your worth. You deserve something, and someone, great. You deserve to feel strong feelings, respect, and admiration reciprocated back to you. You deserve someone who will make every attempt to communicate honestly and effectively with you. Every heartbreak brings you one step closer to finding a relationship where you’ll feel loved, safe, and appreciated. Don’t stop until you find it.

x Kelly

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