DEAR DR. NERDLOVE: I have a bit of a conundrum that has appeared in my dating life especially considering the times we currently live in. It’s a bit long winded but hear me out.

In short, there are two parts to this story. First, I worry that some past experiences have been giving me some trouble with a current girl I’ve been talking to and don’t want to let my past experiences ruin this. Second, I am also having a sort of issue where I am having a harder than usual time gauging people’s intentions, given the current situation. There is a lot of crossover, and I’m unsure how to proceed.

Let me give you a little background. I’m a 22-year-old guy in college and have spent the better part of the last year turning my dating life around. I’ve had some success, but nothing super significant, and I’m looking for a long-term relationship.

A couple of months ago, I had a major letdown happen and it really brought me down. In short, I was led on for a few weeks and rejected by a woman (let’s call her BY, also a student), ostensibly not because of me, but because BY had been recently dumped by a longtime boyfriend. I had previously prided myself on not getting hung up on any one potential relationship, but with BY, I really “bought in” and got hurt by not asking questions and not being careful. There were warning signs, but I didn’t feel it was my place to dig into former relationships and trauma especially being so recent. I’ve also had clinginess and self-worth issues in the past and was trying to not repeat that behavior. I had felt good about myself and the situation, so this wasn’t much of an issue as it historically has been. Nonetheless, it was on my mind and probably affected my actions.

A short while later, I find out BY is now dating another guy and I feel lied too. Queue a major self-improvement streak and a major recovery. In a lot of ways, I’m in a significantly better place than before BY; things have really improved. In the meanwhile, the world is collapsing due to COVID-19 and everything goes online.

That brings us to the current situation. I’ve met several new people through dating apps and am trying to keep my options open. However, I’ve become much more acquainted with one in particular (call her BR, two years older with a real job), and it’s causing some cognitive dissonance. This is also where my second question comes in, because BR’s behavior has been a little strange.

In brief, BR is not especially prompt at replying to me and displays questionable interest outside of dates. The first date we had was unexceptional, and I wasn’t especially interested either, but felt that there might be something given the right opportunity. I make an attempt to talk to her during the week off the app, but the line goes quiet (just a one off at this point). A few days pass and I ask her out on a second date, which goes much better. It turns out, that me and BR have a lot in common and there is definitely something. It’s also poignant that these are clearly defined as dates by both parties, so at the very least, I can rule out miscommunication. However, despite a newfound interest in BR, the lack of communication outside of dates is making me question if I should pursue this any further (the “f

k yes” rule). It’s a mixed signals question: even though BR seems to enjoy our time “in person”, she doesn’t seem that keen outside of it.

At this point, my question is how should I gauge this situation? What should I do if the no responses (outside of proposing dates) develop into a pattern? Given the current situation, she could just be taking things slow, especially since we’re online only so far. Also, I don’t want to appear clingy by jumping the gun but am also aware of the possibility that I could be a 2nd or 3rd choice and am being strung along. I want to make my own boundaries and self-worth clear and will exit if she is not really interested. How do I clear this up or should I even attempt to continue at all? What would be the best way to approach this? On top of this, I am still dealing with a bit of lingering PTSD from BY regarding really “buying in”. As a result, even though BR seems great, I am worried about getting put in a similar situation (despite needing to if I want to move things along with BR). I love your work and would appreciate to hear your take on this.

Best,

Figuring It Out

DEAR FIGURING IT OUT: First things first, FIO: I’m questioning your framing of the situation with BY. What you describe doesn’t sound like you were being “lead on”; it sounds like you were making a lot of unfounded assumptions that didn’t have any basis in reality. Unfortunately, it can be easy to let yourself get caught up in the moment and allow for what Dan Savage calls “dickful thinking” to color your perceptions. However, BY ultimately isn’t responsible for living up to the expectations you had built up in your head. If the issue was that you weren’t asking questions (like, say, “is this going somewhere?” and “are we a thing?”) and not that she was lying to you (“yes, it is and yes we are,” or “maybe, let’s keep trying and see”) then this is less your being betrayed and more of a learning experience. Like I said to Three’s Company yesterday: you have to date with intent, instead of letting things “just happen” and hoping that it’ll all work out.

Now I bring this up because it seems like you’re making similar mistakes with BR. It seems like you’re spending more time reading the tea leaves than you are actually trying to get answers. If you want to know what’s going on, the best person to ask isn’t a mouthy bastard with an advice column, it’s to use your words and ask her. It could be, for example, that she simply doesn’t like texting or messaging apps. She might be someone who prefers actually talking on the phone (a rarity in this day and age, I realize). Or it could be that she’s simply not that communicative a person, especially this early on. It could be that she’s the type who doesn’t put much effort into relationships and tends to be the more passive partner. Or it could be that she’s just not that into you and this is how she shows it.

I don’t have the answer to this; BR does. That means that she’s the one you’ll need to ask — and apparently in person, if she’s this uncommunicative via text. And if she doesn’t have an answer for you — she may well not know why she’s like this, she just knows she is — then you’re going to have to decide if that’s the kind of relationship you want.

But whether you try to make things work with BR or move on to someone else, you need to stop taking as passive an approach to dating as it seems that you have been. You’re going to have to be willing to be your own advocate in a relationship and ask questions. If you’re afraid that calling attention to an issue within the relationship — even if it’s as simple as “are we a couple?” — because you worry that it’s going to tank the relationship… well, that’s a relationship that probably needs to be tanked. And while having things fall apart because you wanted clarity and asked for what you need can sting, it’s far less painful than the anxiety and stress that comes from trying to divine meaning from silence in a seemingly ambiguous relationship. Certainty is far more comforting, even when it’s negative, than being unsure and having no idea what to expect.

Date with intent FIO. Be up front about what you want and what you’re looking for. If you feel like there’re mixed signals, then put in the effort to straighten them out and ask. And don’t let your hope for what you want blind you to what’s actually happening.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I tend to meet women on Tinder and date a couple at a time. Five years ago, I did this because while I could be charming for a date or two, soon enough the realities of my then pathetic life would shine through. The reaction was girls tended to like me less the more they got to know me. Most ghosted me within a month. To counter this endless loss, I kept a steady stream of new dates coming.

My life is a lot better now. I have a job, am no longer chronically ill. I am also in therapy to work on myself. That has affected my dating life. Just as before, I meet women online and it goes pretty well. The big difference is that right around the 3-5th date mark, when they’d normally show diminishing signs of interest, women are instead sticking around. If anything, I can tell they like me more and more. This makes me happy in general, but has led to some new problems.

I currently am dating three women and occasionally go on other Tinder dates. None of these girls know about one another. Each relationship is “real” in that we go on dates and hold hands and all that, but none have escalated much emotionally.

I’ve never told any of them I love them, and I certainly never said to any of them we were exclusive. I keep expecting one or all to bring it up, but they never do. I have no idea If they are seeing other guys or if they think we’re monogamous. I feel like had I met them knowing they weren’t gonna bail, I would have been more honest earlier.

I’m aware the easy answer is “just ask them!” But I really don’t want to. If one does ask me, I plan to be honest but vague with them (“I like you a lot, but I’m not interested in monogamy. I don’t expect you to follow any rules, either.”) I’m perfectly fine with a don’t ask don’t tell arrangement. But I worry that if I bring this up myself , I’ll make things awkward or tank a relationship I like.

I don’t have much of a game plan because this is all new to me. I like all three girls, but if any found out and forced me to either date just them or end the relationship, I would end the relationship. I’m coming to believe I will never want monogamy. If anything, I suspect I’d be happiest with a “real” wife or girlfriend that 98% of the time we would look normal. The caveat being we both date/bang other people.

It’s hard to consider myself some cheating playboy because there’s no lie. I certainly wasn’t cheating when we’ve known each other for two weeks. Or a month. But it’s like month six now and it feels like a line has been crossed. Has it? Who decides that and when? If this all ends in disaster, I won’t feel like a scumbag, but I will feel bad for hurting a girl’s feelings.

Interested in your thoughts,

Three’s Company

DEAR THREE’S COMPANY: First of all TC: congratulations on all the progress you’ve been making. You’ve come a long way, and your determination is admirable. You should be proud of everything you’ve achieved; it’s taken a lot of hard work to get there and that’s amazing. In fact, that progress is precisely why you are dealing with what we in the dating advice business call “a quality problem to have”. There are far worse things in this world than to have reached a point where your problem is that you’re having to juggle multiple relationships.

Now with all that being said, let’s talk a little about some best practices when it comes to dating multiple people… and where you’re inadvertently tripping yourself up.

The first issue is how much you may be borrowing trouble from the future. Right now, you’re going on dates and “holding hands and all that”. If I’m perfectly honest, it doesn’t sound like you’re at a point where you’d actually need to worry about how to bring up the “by the way, I’m dating other people” conversation. If holding hands is towards the upper limit of your physical intimacy with these women… well, honestly, I think you’ve got a bit before you have to worry about having any sort of Defining The Relationship conversation. Now if you’re sleeping with these women — whether just one or each of them — then the clock is likely ticking and you’re going to be having these conversations sooner rather than later. But if you haven’t reached that point with them, then I think you’re at a stage where you don’t need to be preoccupied with how to bring it up.

The second issue you’re having is how much you’re letting these relationships “just happen”. Right now, it seems like you’re trying to surf the ambiguity wave, having Schrodinger’s Relationship, where you’re both exclusive and not at the same time and you’ll only know which when she calls the question of “just what are we, anyway?” That’s not the coolest move to pull and one that has a high possibility of ending up with one or more women feeling tricked and upset by the fact that you were dating others. And let’s be real: you know that already. That’s why you’re doing this. You even say it yourself:

But I worry that if I bring this up myself , I’ll make things awkward or tank a relationship I like.

Well… yeah. That’s likely to happen. But hiding something that might be a major dealbreaker because you know that it’s likely going to be the end of the relationship is really not cool. Plus, to be perfectly blunt, it ain’t like it’s going to feel like any less of a betrayal if you hide it for longer.

Now in fairness: I’m a believer that folks should assume non-monogamy and non-exclusivity by default until you’ve had an actual conversation on the subject. While it isn’t fair for someone to try to hold you to an arrangement that you didn’t consent to — or even know that you were involved in — it’s also not cool to let folks assume that you’re their one and only when they want or expect exclusivity. “Well, you didn’t ask,” may be technically true, but it’s not going to be much of a guard against feeling hurt or betrayed and realizing that they were investing time and energy in a relationship that ultimately wasn’t one that they wanted.

This is why I’m a fan of making sure everyone is on the same page early on, and that you’re both clear on what this relationship is. It doesn’t mean that you need to say “Hey, don’t forget, we’re totally not exclusive”, but it is important to check in on occasion and make sure everyone understands what’s happening — even if it’s just to say “hey, FYI: I’m not monogamous, and I don’t expect you to be either.” The more dates you’ve been on or the more intense your connection is, the more that conversation is going to be called for. It’s one thing if you’ve been out three or four times. It’s another if you’ve been seeing each other regularly for months. You may not have said the words, but with social and cultural mores being what they are, it’s not an entirely unfounded assumption on her part either.

So it’s best to be dating intentionally and actively looking for folks who are at least open to the same things you are… which in this case is non-exclusivity. As a rule of thumb: this is something best brought up by date three, or prior to sex, which ever happens first. While I know some folks believe in disclosure immediately — and that may be more appropriate if you already have a primary partner — giving it a few dates first lets them get to know you as a person instead of the image of a polyamorous or non-monogamous man they have in their head. But it’s still a conversation to have early on so that both of you aren’t wasting your time.

This doesn’t mean that people won’t still get the wrong idea, or only hear what they want to hear, but at the very least, it’s considerate and ethical.

Frankly, leaving it ambiguous until someone else brings it up is a coward’s move. Date with intent, my dude. You’re going to need to be an active participant in the relationship and actually help steer things, or you’re going to keep ending up in places you never wanted to go.

The third issue is that it doesn’t sound like you’ve done much in the way of research about ethical non-monogamy and how to manage open or polyamorous relationships. I would strongly suggest that you start doing your due diligence before getting any more deeply involved with these women. If you’re going to want a non-monogamous commitment, then you need to know exactly what that entails and how to maintain it.

So here’s your homework: check out Opening Up by Tristan Taormino, The Ethical Slut by Janet Hardy and Building Open Relationships by Dr. Liz Powell (full disclosure: Dr. Powell is a personal friend of mine and has been a guest expert in my column before). Read these and start to learn about precisely what it takes to start and manage an open relationship, as well as how to talk to your partner(s) about it.

But I can’t emphasize this enough: if these relationships are progressing to the point of seeing them regularly, these are conversations you’re going to need to have. Leaving it up in the air in hopes that it will never come up is how you get dumped so hard your grandparents divorce retroactively. And hiding it in hopes that you can thread this particular needle without actually discussing it and running the risk of ending a relationship is how you end up in the special hell. You know the one.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I really like the advice that you give because it’s fair and takes both male and female perspectives into account. I need some help here. I started off dating a younger guy, J, casually about a year and a half ago after splitting from my ex-husband. For the first like 9-10 months things between us were very casual, I’d show up, we’d have some drinks, get physical, and then I’d go. This arrangement worked well for both of us and I enjoyed it. We had no commitments to one another whatsoever. I left for a few months to work in a different city and was unfortunately date raped. J was supposed to visit me, but I called him almost immediately after my experience and told him he shouldn’t come because I was just too messed up. Apparently, for J, this was the wakeup to realize that he had real feelings for me.

A couple months later, I get back home and we start up seeing each other again. We attended a festival together and had a great time and got really close because of it. He told me he wanted to start dating me, which freaked me out and caused me to run and hide for the next month and a half. During that time I got really flakey. Admittedly it was the wrong way to handle that, but I was really struggling to deal with things. I was just working some things out from my assault and couldn’t get physical or emotional.

Once I began to feel better, I started seeing him again. However, it was very different and both of us developed deep feelings for one another. At some point he tells me he is in love with me. After a couple months of doing that, he asks me to be exclusive with him. Throughout all of that time he treated me with kindness, respect, and understanding. He was very supportive when I was dealing with PTSD issues, although he was hurt that I ghosted him for a while which I apologized for. All this is to say, I thought that based on his behavior and words that he was loving, sweet, and gentle (albeit a supporter of the opposite political party of me, and we are both very politically opinionated).

About 5 months into our exclusive relationship I see messages on his phone to his friend saying things like “I can do better” than this girl and “I really love the girl and she’s given me no reason to break up with her.” Some these exchanges with his friend involved times where his friend encourages him to simply cheat on me; J would reply with “I would, but she’s been cheated on before and she’ll find out.” Well, this infuriates me and I break it off with him immediately. Unfortunately, I’m also studying for a very rigorous exam and I am stressed out to the max, so I take the break-up really hard. He meets up with me and tearfully apologizes and tells me he was wrong, and he can’t live without me. I decide to give him another chance.

Then I discover that he has previously been very involved in this Red Pill movement. In fact, he’s met people he chatted with on Red Pill chatrooms in person. After doing a lot of research on the Red Pill, it becomes apparent to me that his previous comments about me to his friends stemmed from this philosophy. He assures me now that he does not agree with the majority of what that philosophy preaches, and really he’s only interested in stoicism and self-improvement which he learned from that site. I’m skeptical because he remains in contact with those friends and still checks out the subreddit frequently. I’m not even sure how someone who followed that philosophy could have ended up with a person like me; very liberal, outspoken on politics, possesses a doctoral degree, proudly feminist, very assertive and not afraid of confrontation.

It’s been really hard for me these last weeks because I feel so torn. On the one hand, I abhor the Red Pill philosophy and I am very concerned that J either used these techniques on me in the past, or will use them in the future to try and trick me. Admittedly, I’m now on high alert so I doubt that’ll happen. On the other hand, he has been such a source of support and love in my life, we have a great time together, have similar senses of humor, even now the sex life is incredible, etc. He has literally been taking care of me day in and day out while I study for this exam (which I have been doing everyday for the last 8 weeks for 10-12 hours per day), and I have truly not been easy to deal with because the stress of this exam is causing me extreme anxiety (and is doing the same thing to my friends who are also studying for the exam, so I’m not alone in feeling this way). He’s been visibly trying to show me that he values me and wants to be in a relationship and is willing to do what it takes.

How do I reconcile dating someone who (1) at one time told his friends he thought he could do better, but now has backtracked and after our split has literally come back to me saying that it made him realize he needs me and wants me in his life more than anything or anyone, and (2) who has such different views about social relationships between men and women? I love this dude and I want to be happy, how do I do both?

Twice Bitten

DEAR TWICE-BITTEN: I have a few questions, TB, for you and for J.

The first is simple: if all he wants is self-improvement and/or lessons in stoicism and “disagrees with so much of the philosophy”, then why in pluperfect f

kery is he still there? There are plenty of other communities that he could join, ones that don’t involve deeply misogynistic and manipulative bulls

t. The second would be how, exactly, he can reconcile being in love with you and wanting a relationship with you and still being friends with people who keep telling him to hurt you. It’s one thing to have different groups of friends who may not get along. It’s another entirely when one of those groups is actively telling him to ruin a relationship that he supposedly values.

This, incidentally, leads to my third question: which version of him are we supposed to believe: the one where he says that he loves you and values you and wants to make this relationship work, or the one where he says he’s only with you because you haven’t given him some sort of casus belli that would justify his leaving you? Who’s he lying to, you, his asshole friends or himself?

He’s already jeopardized this relationship once. The fact that he seems to be back on his bulls

t doesn’t exactly lend credence to the idea that he’s realized he’s wrong and he’s going to do better. It’d be one thing if he was trying to leave all this behind and was just struggling with breaking years of habit. But the fact that the Red Pill community is still such a big part of his life – even if it’s “just” the self-improvement bits – is a different matter. He may love you… but it doesn’t really seem like he respects you.

Were I in your shoes, I’d want to have a very long, drawn out talk about all of this – why he joined the community in the first place, why he’s still part of it, why he’s still talking to people who tried to ruin things between you and what, exactly, he’s going to do about it going forward. I would also say that it’s on him to show that he can be trusted. He’s neck deep in some toxic f

kery and while you can sometimes manage to filter out the good from the bad – that’s a major part of my secret origin after all – there comes a point where it’s worth asking why it’s so important for him to keep trying to pick the nuggets of corn out of all that s

t. He can find other resources for the self-improvement if that’s what he wants, even communities that promote positive masculinity and camaraderie. They’re out there, if he wants to seek them out.

And that’s a mighty big if.

If he is trying to leave it all behind, then I support that. I honestly believe that it’s important to acknowledge that we can grow and improve over our s

tty pasts. But he needs to show that he’s doing that. And if he can’t – or won’t – leave it behind, or you can’t bring yourself to trust him… well, as the sage says: sometimes love just ain’t enough.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com