How Do I Get Better at Dating… When I Can’t Actually Date?


Dear Dr. NerdLove: How can I get better at dating, without actually dating? It’s a weird question but my situation feels weird.

I’m a 37 year old guy, and I’ve never dated in my life. I ended up marrying my best friend straight out of college. Not necessarily something I’d advise my past self given the chance, but it made sense given our information and beliefs at the time. We’re both from conservative families and thought we should save sex until marriage, which tends to accelerate things. Yeah, I know. What can I say? We were 21 and we didn’t know any better.

Fifteen years of ups and downs, and two kids later, we’ve made it work so far. But everything’s changed. Over the years, my spouse has come out successively as bi/pan (with a preference for women), trans/nonbinary, and nonmonogamous (at a philosophical level: nothing’s happened so far.)

I’ve been strongly supportive throughout, and processing all this has actually been a major bonding point for us. For them, having the option of a potential non-straight-guy partner has been extremely important and empowering, whether they acted on it or not. But things between us have also been rough. Some issues probably related to sexuality/identity, some much more mundane. My spouse is a naturally slow-moving, domestically-focused introvert, so for the most part a lot of this has felt like an academic exercise. But I am feeling a lot of relational stress — I have a lot of unmet needs, on several fronts, and I know they feel the same way. Plus a host of common relationship issues.

At this moment, I don’t think there’s any real possibility of acting on any of the nonmonogamy stuff. I wouldn’t feel comfortable being the one to initiate that. Everything I’ve read indicates that for it to work, communication is of paramount importance. And quite frankly, at the moment, our communication is complete shit. Straight up not good. We’re both in therapy individually. We’ll start couple’s therapy soon, most likely, and I really hope that will be helpful. I realize the actual content of our relationship issues is likely outside the scope of what you can advise on.

But as I see it, there’s only 4 options. We could separate. We could establish an actively nonmonogamous relationship. We could maybe figure stuff out and end up happily monogamous. Or, and this is the only option I will NOT accept: we could keep kicking the can down the road and remain unhappily monogamous.

Hence my question. For two out of the three acceptable options, learning to date and form new relationships is going to be important for me. And even in the happily monogamous outcome, I think, becoming a “datable” person will make me a better human and a better spouse.

So how can I start to think ahead, and build reps on being a person who is good at building and maintaining relationships, without the opportunity to actually hit the world and practice?

Thanks so much!
– Confused Quasi-Dater

OK, CQD, let’s talk dating and practice. First things first, it’s good that you’re already starting couple’s therapy. This is going to be helpful on a number of levels; at the very least, having a third party to help mediate the conversations you and your spouse are having (or need to have) may make it easier for the two of you to be heard and understood.

You’re also correct that yes, communication is vital. It’s important in general, but if you’re going to open up your marriage, then good, clear, open communication is going to be the bedrock that everything else rests. And I’m very glad to see that you recognize that your communication needs work; that sort of awareness and judgement is going to be one of the most important factors going forward, regardless of which way you and your spouse decide.

Now, there’re a few things to keep in mind. One of them is that opening up your marriage doesn’t mean that you need to throw the doors wide open, never to be closed again. In fact, if you were to start looking into ethical non-monogamy, I’d suggest that you and your spouse may want to start slowly. It’s hard to know how you’re going to feel when you know that your spouse is being intimate with someone else – whether that means sex or not – or how your spouse will feel when you are with someone else. So one of the things you may want to consider is taking baby steps into that particular pool.

For many, this may mean saying that sex is off the table but kissing someone else is. Or it may mean both of you going out and seeing how it feels to see someone flirting or dancing with your partner. To be sure, being ok with those lower tiers of intimacy or affection isn’t a guarantee that you won’t be dealing with some complicated and possibly uncomfortable feelings if/when things go further. However, taking things slow will both allow you to get acclimated to the idea and to see that opening up your marriage doesn’t mean that your spouse cares less for you than they did before.

Another thing to consider is that just because you open things up, that doesn’t mean it’s open forever; you can say “hey, I feel like we need to close things down for a bit” if issues come up or you or your spouse feel like you have needs that are being neglected. However, this comes right back to “make sure you have strong and clear communication” and a focus on actually identifying and resolving problems. I’ve seen ENM couples who used requests to close the relationship as a way of continuing to control who their partner does or doesn’t see, or otherwise holding it as a weapon in other conflicts.

A third thing to consider is to that you will want to start doing your due diligence on open marriages now. Even if opening things up is in the distant future or strictly theoretical, starting to do your reading will be incredibly important. It’s a lot better to have the info at hand before you start, rather than playing catch up later, especially if you’ve stumbled into habits that may be counter-productive and need to be unlearned. I’d recommend starting with Tristan Taormino’s “Opening Up”, “The Ethical Slut” by Dossie Easton and Janet Hardey, and “Building Open Relationships” by Dr. Liz Powell.

(Full disclosure, Liz is a friend of mine and they’ve guested on a few of my columns)

Of course, it can seem a little weird that I’m talking so much about ethical non-monogamy when you and your spouse haven’t decided what comes next and any movement this direction is in the future. But I bring it up because the practices that make it possible for a couple to open up their relationship are also the practices that make you both better at closed relationships – communication, trust, sharing, checking in with one another, being mindful of your needs and your partners’ needs, being willing to actually say what you need and to listen to what they say and so on. Even if you choose not to open things up, these can go a long way towards helping improve things in your marriage.

They’re also going to be helpful in being a more datable person who’s good at building relationships.

Which brings me to a misconception I think you have. I think some of what you’re worried about aren’t really relationships, per se, but the basic mechanics of meeting folks, asking them out on dates and so on. And honestly? I know it’s been a while since you’ve been in the dating game, but I can promise you that you already have the mechanics of what you need.

Here’s the thing that I think you’re missing: you can build and maintain relationships – and be known as someone who’s good at this – without cheating or needing the relationship to be open already. The thing that folks often don’t realize is that relationships are relationships, whether they’re romantic or not, platonic or not. A romantic or sexual relationship isn’t some strange beast that follows different rules than all the other connections in your life. Friendships are relationships, after all. Work relationships are also relationships. The same things that make you a good friend – someone who can be trusted and relied upon, someone who’s considerate and caring and so on – are the things that make you a good partner.

Going out, meeting people and building connections don’t change drastically between making friends or finding a potential date. The skill sets are ultimately the same, when you get right down to it; the only difference is the intent and desired outcome. Don’t forget: we very rarely start a relationship with someone based on love at first sight. More often than not, our romantic relationships develop over time – going from strangers to acquaintances, acquaintances to friends and friends to more. This is why, even in the far flung future of 2022, a plurality of people meet their romantic partners through shared activities or mutual friends. Propinquity and who’s around you have much more to do with who we hook up with than pure random chance.

If you know how to talk to people and make friends, you’re already 90% of the way there. The remainder is mostly about knowing how to take things further… and fortunately I have a massive archive to help you learn these skills, and private coaching options if you need more direct help.

But I want to circle back around and stress that before you decide how you and your spouse are going to pursue things, you should make sure to work on your relationship with them, first. The stronger a base you two have, the easier it will be to make your future relationships work, whether you open up or not. Communication, knowing how to express your needs clearly, how to listen to your partner and establishing the baseline of trust and affection will be vital. Without those, opening up your marriage will mostly just speed run its ending… and it’ll make that ending much more complicated and unpleasant for everyone.

Oh, and one more thing: there’s another option that you may not have considered: you and your spouse can define your marriage and your relationship however you want. Even if your spouse decides that they’re more inclined towards women than men, you don’t necessarily need to separate. If you and your spouse are good co-parents and have a strong connection of affection and respect for one another, even if you aren’t necessarily “in love” the way you were at the start, you could opt for a companionate marriage, where the the sexual and/or romantic connection isn’t necessarily a priority and you’re allowed to have those needs met outside of the marriage.

Or there are other arrangements that you and your spouse could make. You could, for example, stay married but have separate homes, if you prefer (and can afford it). Having your own separate place would make it easier, logistically, for you two to conduct your affairs (pun intended), without necessarily being up in each other’s business, especially if you decide your marriage is more companionate. It’s not necessarily easy or something that everyone can do, but I *do* know couples with children who chose to get separate apartments or condos in the same complex; this allowed for them to co-parent easily but have their own space without making things more complicated on the dating front.

But overall, I think you’re in better shape than you realize. You clearly have a good grasp on what needs to be worked on and I think you’ve got your priorities in the right order. Focus on fixing your communication first, then look to next steps after. Regardless of whether things improve or you transition to a new sort of relationship, this will make everything better, for you, your spouse and your children.

Good luck.


Hi again, Doc!

I know updates aren’t the most common, but I was reading your column re-runs and it made me realize how far I’d come since I wrote to you.

Long story short; took your advice and it worked out. Thanks so much!

Longer story: We kept the lines of communication open, but the progress was not linear. His friend continued crossing boundaries in escalating ways in 2020 and he kept shutting her down. He repeatedly told me to say the word and he would stop hanging out with her, but I firmly left that choice to him. They had a fight in January 2021 and took a break for a month and he realized how much less toxic his life was without her, and decided to keep her out of his life.

Sadly, other problems boiled up with his family and our relationship at the same time and I did give an different ultimatum: weekly therapy until the therapist says otherwise. In a true miracle, he found a bilingual therapist who specializes in his and our specific issues. I would be truly, literally be surprised to death is there are 5 other people like her in the world. And she had availability.

He attended the weekly sessions from January 2021 to September. I attended some sessions for couples therapy but it was largely his journey. One day in May he called me up afterwards and profusely apologized for not understanding the difference between a friendship and a committed relationship–he finally understood the color blue, as it were! He attended monthly thereafter until February 2022 and now he says if things ever get overwhelming, he will make an appointment.

As you said in your initial response, it was supremely frustrating that there was nothing I could do. I also had to wrestle with my own surprising feelings of anger when he would have a breakthrough with a therapist after one conversation…that was identical to the multiple conversations I had previously had with him. Your advice helped me to let the feelings pass and focus on the journey, not how far away the destination was.

We now joke that our relationship can be split up into two eras (B.T. and A.T). I feel incredibly lucky that my partner has emerged from this stronger and healthier, that we now have a rock solid relationship with steel foundations, and that we now both have better emotional intelligence fluencies that we use to lift each other up.

Understanding that no relationship is truly perfect or conflict free, I can proudly say it is perfect for us and I look forward to tackling our future conflicts together, as a team. Thanks again for helping us get here.

Found and Content

Thanks so much for writing back and letting us know how you’re doing, FaC! I’m glad you and your sweetie’ve been able to make things work and find your way to a stronger, happier relationship!


A couple more things before I go.

First: I’ll be doing a live Q&A for my Patrons on December 29th, with Q&As open to my general audience coming in the future. If you’re interested in taking part, consider supporting the site by becoming a patron at; patron questions will get priority in future live streams.

Second: As the we’re coming to the end of the year, I have a couple requests. First, since January is National Break Up Month, I’m putting out a call for questions about ending relationships: when you need to end it, how to end a relationship the right way, when a relationship can be fixed and how to handle break ups – either as the dumper or the dumpee. As always, submit your questions via the submission form, or send them to with “National Break Up Month Question” in the header.

Third: Since that’s also a hell of a downer, for February – especially for Valentine’s Day – I want to hear your Relationship Wins. Tell me about ways you and your sweetie turned things around, what you’ve learned about making things work, how you two solved problems together or otherwise made each other’s lives better. Let’s share some happiness and spread hope, especially in a month when a lot of folks may feel at their lowest. Who knows, maybe you’ll see your story featured here.

This post was previously published on and is republished on medium.


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