Should I keep dating him if he isn't ready for a relationship?

If I walk away, am I doing the smart, self-protective, mature thing or am I closing myself off to potential love?

Here’s The Thing is an advice column/newsletter where I mostly beg people to either stop dating someone or to ask their crush out. Or I talk about weird things that came to my mind that no one is paying me to write about. I can never decide if I should capitalize the “the” in Here’s The Thing or not; apologies on lack of consistency. 

You can submit your own question—or yell at me about how I’m wrong—by emailing me at


I've been dating a man I met on Bumble for just over two months. Because of COVID, we had a conversation fairly early on about who was in our bubble and decided we wanted to date each other in person/make out/have sex so we committed to keeping it between us and said that if either of us started feeling like there was someone else we were chatting with on the app that we wanted to see, we would talk to the other person about it first and let them know. This was our way of being COVID exclusive without feeling like we were jumping into anything too serious too soon. I should probably also mention that he is recently divorced and has his kids half the time. As someone who has also gone through a divorce (albeit quite a few years ago), I remember how that felt and kind of assumed this meant he was not going to be ready for anything really serious yet. That felt fine with me, as I eventually want a long-term relationship but prefer after being hurt so much to take things slowly and not jump into anything.

So, here's the thing. I realized the other week I'm starting to develop feelings for this guy. Of course I am! We have great conversations for hours, he takes me on real dates, he keeps his commitments, he makes me laugh, he is great in bed, he is an involved father, he is thoughtful and kind and smart, etc. The other night we were talking about how we would both be eligible for vaccines soon and I wondered aloud if the vaccinations and things opening up would impact our dating situation. I told him that I was starting to really like him and wasn't as interested in talking to or dating other guys. And I asked how he was feeling about everything and if he was going to be interested in getting out there and dating multiple people once he had the chance to do so for the first time in 15ish years. He was very honest with me and said he didn't know what he wanted and that he would have to think about it. He said that it had only been less than a year since the divorce and that he had been married a long time. He said he wasn't sure whether the way things were between us (e.g., us exclusively seeing one another) was primarily because of the COVID situation or primarily because he really liked me and enjoyed spending time with me. 

Of course none of this was what I wanted to hear (I was hoping he would say that he hadn't been looking for a serious relationship but I was such an amazing woman that he wasn't going to let me go just so he could date around for a bit and re-live his early 20s). But I wasn't surprised. I thanked him for being honest with me, and we decided that we would revisit the conversation in a few weeks after he has time to think about it. I told him that everything he said made sense to me but if he decided he wanted to see other women, I would probably have to step back to protect myself. 

As I think about that conversation and the next one we may have, what I keep focusing on is that, no matter what he decides, which is out of my control, I need to figure out what I want and what my boundaries are. I feel like a lot of advice out there is that if a man wants to be casual, a woman needs to walk away to show her value and her standards. But there is a part of me that thinks, well, I really like this guy and I like what we have. Would it be so bad to keep dating him to see where things go? Could I also keep casually dating others while dating him and see what happens? As someone who does not have much experience with casual dating (I like to date one man at a time and then am all about those monogamous, long-term relationships), part of me wonders if it would be good for me? Another part is worried I would get hurt if I keep seeing him, knowing he is also seeing other people. I do not have super strong feelings for him yet, but I definitely have some feelings and I know that if we continue seeing each other, they will only grow. 

If he decides he wants to keep it more casual and I decide to walk away, am I doing the smart, self-protective, mature thing or am I closing myself off to potential love just because I am scared of the uncertain, messy part of dating? 

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There’s virtually no way to say this without coming across like a condescending dolt, but this letter was so mature. I really commend you on how well you’ve thought this through. You’ve perfectly gotten at what the issue actually is (what you want), what isn’t in your control (what he wants), and what outside pressures might influence you (the stories we tell ourselves because of society). That all makes it a whole lot easier on me to come down on a side of this. And, as a bonus, I think that will make it easier on you to actually figure out what you want because either a) you mostly agree with what I’m saying or b) you think my suggestion, when written out, is actually foolish and miserable and you reject it and do your own thing. Beautiful all around! Here we go!

Personally—and as ever, my opinion is only given preference here because I’m the author of this newsletter and not because I’m especially right—I would keep dating him.

I think you’re correct that a lot of advice tells women to walk away from anything less than Perfect Partner Who From the Get Go Wants Long Term Commitment With You and Only You. Which, if that’s what you’re looking for and only what you’re looking for, that’s great—boots, start walkin’! However, I think there are a lot of other gradients of relationship out there that are valid and valuable that take time to unfurl. I think a lot of the advice to women which is often to COMPROMISE NOTHING EVER leaves us with, well, nothing a lot of the time. It’s frankly unrealistic.

To be clear, just in case anyone is confused I do not think you should compromise on boundaries. I don’t think you should “settle” for people who are meh because that’s the best you’re gonna get and that’s what you deserve. I OF COURSE do not think anyone should be with or stay with a partner who is harmful, hurtful or abusive because “no one’s perfect.” I believe strongly in deal breakers and red flags. I’m just saying that you don’t need to have a Fabergé egg of a relationship for it to be worthwhile; the answer isn’t perfection or nothing.

Here is the root of the root and the bud of the bud and all that: you’re going to get hurt by this situation. There is no way out. Either you get hurt 22% now because you break it off early. Or you get hurt 48% in eight months when he decides to break things off with you and date someone else. Or you get hurt 79% in two years when things get hard with you being a stepmom-figure to his kids and you both agree to end it. Or you get hurt 99.99% in 50 years when he dies in your arms at the hospital. (The 0.01% that doesn’t hurt is that you don’t miss him leaving wet towels on the bed). You’re going to get hurt when this is over because that is human. In fact, I would argue that that’s the good shit! It’s the proof that someone has become meaningful to you in this world, which is Kind Of The Whole Point.

However, when thinking about the amount of pain you want to go through for this guy, you have to bear in mind that the amount of pain you set yourself up for is directly proportional (not equal, but proportional) to the amount of joy and love you’re going to feel. I suck shit at math—I literally cannot figure out what time zones are, for example—but that is the very very obvious math of loving people. The more you love them, the more you get hurt. So I think this idea of protecting yourself from feeling pain is, frankly, a fool’s errand. You’re going to get hurt if you stay; you’re going to get hurt if you go. The question, I think, is how much good stuff do you want to have first.

[Of course, if you know for a fact that you are in a terrible place to recover from pain, or if you feel like one more big breakup is going to break you as a human right now, then you know that what I’m describing isn’t worth it. That doesn’t seem to be the case from your letter but: you know you best!]

The truth is you don’t know how this is going to play out. You don’t know much at all, and neither does he! Maybe he tries to set up dates with other people and figures out how hard and awful it is to date. Maybe he meets someone right away that he wants to start a relationship with. Maybe he figures out that he’s not ready at all to date. Maybe you meet someone else while dating around. Maybe you reach a point down the road where you feel like you gave non-exclusivity a shot and it worked for a bit, but now you’re at a point where you need him to either commit or not. Maybe you two realize that you aren’t as compatible as you thought and his penchant for retelling that one story about the time he met Dave Chappelle is getting old.

As cliched as it is—and it’s very cliched—I think it’s much easier to regret things you don’t try than things you do. That’s just kind of the reality of a life where you get 80 years if you’re lucky to pack in all the fun/love/anguish/ice cream sandwiches/heartbreak/joy. I think that he would probably regret not trying to date other people after his divorce (which is fair, if a frustrating truth for you in this moment). Similarly, I think you might regret not giving this a bit longer.

I don’t think you should be waiting around for him to figure out what he wants, sitting by the phone with a clear schedule hoping he realizes it’s you, it’s always been you. I think you should keep moving forward with your own life and with your own dating. I think you should try dating other people as well if you feel interested in that. I think you should keep building out your life with friends/family/work/sports/drugs/hobbies/pets/whatever. Obviously, you’ll have to be watchful of the dynamic so that it doesn’t become him deciding unilaterally what you two are and when you two see one another. But I think you’re emotionally intelligent enough to handle that. I trust that you will get out of the relationship if it starts giving you less joy and more pain—and you should trust yourself, too!

If there is still a potential for fun and happiness with this person, I do not think you need to end things for the sake of self-preservation or to make some point about what you deserve. I don’t think that him wanting to explore other things is actually about you and how good of a partner you are at all, as difficult as that may be to internalize and believe. It’s just that life is short and hard and none of us know what we’re doing and we’re all trying to pack as much good stuff in as we can, but we’re also pretty bad at that. I don’t think this is your only shot at love, I don’t think that by walking away you’d close yourself off to anything. I just don’t believe you have to walk away yet.

So, that’s my recommendation. But again, if this sounds hard or bad, you can ignore this letter and end things with him now! You will know when things aren’t worth it! I promise.

You can submit your own question—or yell at me about how I’m wrong—by emailing me at