DEAR DR. NERDLOVE: When is the right time to ask someone out? Is it ok to ask a person for their number when you’ve only just met them? What if you’re not sure if they’re flirting with you or not?��I’ve had a lot of conversations with people where it seemed like maybe they were flirting with me or like we had the beginning of a moment, but I would always chicken out and not say anything when we were done and then I would regret it afterwards. Now I’m older and still single and I’m tired of feeling like I’ve been missing out on chances. Is it ok for me to just make a move, even if I’m not 100% sure that the other person is flirting with me or not? 

Tired Of Missing Out

DEAR TIRED OF MISSING OUT: This is a question where the answer is “That depends…”. Now, I get it: that is both unhelpful and profoundly unsatisfying an answer. But the fact of the matter is that, as much as we might prefer it, there aren’t a lot of hard and fast rules as to when is the ‘right’ and ‘wrong’ time to ask someone for a date or their number or what-have-you. For every rule, there’s someone who has broken it successfully, and plenty of people who follow the “rules” perfectly but without success.  Most of what we have are best practices, general rules of thumb and a few situations that are a “best not” – and all of them are influenced by factors like context, social skill level and experience, and circumstance.

The harder “don’t’s”, for example, tend to be about safety and power. A boss hitting on their employee is an example of a massive power imbalance; the boss may have the best and most honest of intentions, but they’re still a person who can decide whether or not their employee has a job. This puts a lot of pressure on the employee to say “yes”, even if the boss would never exploit their power that way.

A context where the answer isn’t “no” but “not the best idea”, on the other hand, is one where the odds of misreading things are higher. People in service industry jobs or jobs that rely on tips, for example, have an incentive to be nice or even flirty with customers. A bartender who flirts a bit with a customer is more likely to get a bigger tip when they close out, as does a waitress who leaves a doodle of a smiley face and a “thank you” on the bill. A dancer at a strip club is motivated to encourage customers to buy private dances and an OnlyFans model will tease and entice subscribers to buy videos or services they offer. They have a strong financial incentive to play up to the customer’s desire to help move that along. It’s easy for someone to let horny thinking get out ahead of them and assume that there’s more going on than a service professional/customer relationship.

In circumstances like this, you’re not forbidden from asking them out, but it’s highly unlikely to go anywhere. While it’s not impossible – people have asked out bar staff or waitresses or dancers successfully – it’s better to err on the side of “not”, just so you don’t waste time or risk embarrassment.

It’s also important to be able to read the room. Some places are simply not the time to try to hit on someone or get their number. A networking event or a professional setting is usually not the time or place for trying to make a more personal connection. The same applies to, say, yoga classes or other group events; a lot of people – mostly men – tend to treat them as sex ATMs and end up creating an uncomfortable atmosphere for the people who are just there to work on their flow.

But this is also where social calibration and social experience come into play. There’s a difference between someone who goes to hot yoga or a dance class and acts like a horny hyena looking for a limping gazelle and someone who’s there for the class and is just being social. Talking with folks and making a connection that eventually leads to asking them on a date is very different than someone who’s only there because that’s where the hot people are and couldn’t care less about their Salute to the Sun.

Someone who is very good at reading the room and has a solid level of social skill and experience is also more likely to be able to discern – correctly – when a specific situation is an exception, and the person they’re talking to would be receptive to a date or giving their number. That, however, is born out of experience and the understanding that exceptions are just that – exceptions. If you have to ask if this is an exception, the answer is almost certainly “no”. And if you’re asking me if it’s ok to ask someone you’ve just met out on a date… well, it doesn’t sound like you’ve reached that level of skill yet.   

But if we’re talking about casual conversation with a stranger or acquaintance – one that’s more than perfunctory small talk or a conversation in passing… that can be a little different. If you’ve been having a good conversation with someone in line at Starbucks, or that you just met at a party, there’s nothing wrong with saying “Hey, I’ve really enjoyed talking to you; is it ok if I give you my number?” or “I’ve got to go but I would really like to talk to you again; may I add you on WhatsApp/Messenger/Instagram/$INSERT_MESSAGING_PLATFORM_HERE?”

The key in this case, is that you’re putting the ball in their court. By offering your number or WhatsApp ID, you’re giving them the chance to decide whether they want to take the next step or not. It’s less of an imposition; you’re not asking them to make a decision now, so much as giving them the option of doing so later. It’s a little easier to say “yes” to the opportunity to say “ok, that guy was pretty charming, I’ll give him a text tomorrow” than decide if they want to roll the dice on you right then and there.

A thing to keep in mind is that missing out on opportunities isn’t the end of the world, especially if you aren’t sure there was an opportunity to miss out on. There will be other opportunities, especially if you are making an effort to be social and meet people in general. But if you can just enjoy having conversations with people and vibing with them, you’ll start building the skill and refining the calibration that will make it easier to know when someone’s into you and when someone is just enjoying talking to a stranger and doesn’t want anything more than that.

Oh, and one last tip: if you’re unsure if someone’s flirting… just ask. There’s a minor risk of embarrassment in asking, but the embarrassment from asking and being told “no” is a lot less than the embarrassment of guessing and guessing wrong. Plus, a well-delivered “…are you flirting with me?” can be a hell of a sexy line, especially if the answer is yes.

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:  Thank you so much for selecting my letter (“How Do I Cope With Transforming My Entire Life In One Year” Jan 01, 2026) and for your incredible, compassionate response. You were right, and while I didn’t need a Clarence, I think this still qualifies you for wings. I wish I could adequately convey in words the depth of “seen” that I felt from your reply. I was hurting a lot at that time and it wasn’t easy to get through. It hit a point where therapy and meds almost weren’t enough. I really learned who was willing to show up for me, which was humbling; and I also learned who wasn’t, which was heartbreaking, but necessary.

I’m still recovering from all the changes in my life, and that won’t happen overnight. I’m hoping today that you might help me tackle a completely different issue.

I’ll cut to the chase: I’m an American dual-citizen living in terror of ICE. I am mixed race, and Trump has recently halted Visa processing from a number of countries, including my mom’s country of origin. She often gets mistaken for Chinese (we aren’t) and with Asian hate on the rise since COVID-19, I’m more concerned than ever.

In my previous letter, I mentioned growing closer to some aunts I never got to know well as a child (on my dad’s side, which is the white/American part of the family; my mom and I have always been the only members of her family in the US). And the good news is, I’ve inherited an entire family of self-professed flaming liberals who are all dying to keep getting to know me and supporting me!

The not so nice news is that even though they vote/donate/protest/otherwise are very solidly on the correct side of history…many of them were born in the 50s and 60s and occasionally our conversations are peppered with side comments that are giving that good Old School, Casual Racism I thought I’d left behind years ago. I heard a lot of these types of comments growing up, and while racism is very clearly still rampant in the world, I was surprised to find my dad’s family still in the same mindset in that respect especially since they are so progressive in every other way.

The comments have ranged from mildly awkward such as, “Do you eat a lot of [country name] food? Like they have at restaurants?” to the more problematic, “I think you look American enough not to be profiled by ICE.”

There have been other remarks as well, and even pressure to eat food that is in violation of my and my mom’s religion (my dad is not religious but his family all grew up in a different religion). I genuinely don’t want to deal with these types of comments anymore at this stage in my life (or retroactively ever).

What’s worse is that it turns out that my dad has been subtly isolating me and my mom from the rest of his family all along, and then controlling the narrative to paint us as practically infantile submissives – even in the years when I wasn’t part of the family picture. For example, he’s convinced them all these years that my mom has a language barrier; when the woman I know is a polyglot with an American GED and Associate’s Degree who easily handled all my doctor’s appointments and PTA visits growing up. He’s been seeding Orientalism, Othering, and Asian as Perpetual Foreigner stereotypes in our own family…since the 80s. For literal decades. Present-day, he has openly stated that he doesn’t believe I can be trusted to make my own decisions, or have the right to work and own property in both countries unless he is involved, compares me to other people’s children, goes on about how I’m not responsible enough to be in his will, etc.

I feel like his attitude is frankly dangerous, but I can’t change him. I’d rather turn my attention to people who have my back and believe me. Yet, much of what’s going on seems new to many people who are on my side, and in terms of reconnecting with my family, there are some faux pas that I’d really hoped to never have to explain to anyone again and undoing my dad’s past damage. I’ve been explaining things as patiently and as best as I can in the moment, but it tends to be pretty jarring. I live and work in a relatively progressive area where we have better rights and more representation overall. There’s still racism, but at least enough people have figured out not to say the quiet parts out loud, and social policies are moving in the right direction. I don’t experience the same day-to-day racism in a blue city as I did in a red state. The white folks in my life are all much more open-minded than my dad and really try to listen to me, but I’m not sure they, having never experienced any of this firsthand, understand that some things are not okay to say, let alone the true risk to me from all of this.

For me, anti-Asian racism isn’t new. It literally has its own Wikipedia page, as do the stereotypes I called out earlier. I’ve been living in a post-Korematsu world all my life. I mean, George Takei is still right here. I feel like I’ve barely been staying one step ahead of Trump for at least a decade. I’ve made many life-altering decisions based on his policies, such as getting an IUD in 2017 when he threatened to dismantle the ACA, moving to a blue city with better voter protections and healthcare prior to the pandemic, planning a vasectomy with my partner after the Roe v. Wade debacle, and ultimately getting my hysterectomy which I intentionally scheduled ahead of inauguration day in 2025, etc. So many of my life choices have been the result of politics.

Here’s where I’m asking for your input. Based on past letters where you’ve weighed in on racial issues through a white lens, I think you’ve put a lot of effort and sincerity into allyship. As a person with all kinds of reasons to get disappeared by the government once s--t goes full Handmaid’s Tale, is there anything else I can be doing to help my allies be better allies (without exhausting myself as their personal educator) both on an interpersonal level and in the broader fight against tyranny?

Sincerely,

Somehow, Still George Bailey

DEAR SOMEHOW, STILL GEORGE BAILEY: Alright, I’m going to be real here – I’m a loudmouth with an advice column, not a community organizer or political activist with a lot of on-the-ground experience in de-radicalizing people, educating folks about anti-racism or otherwise someone who’s in a position to say “here’s how you overcome generations of systematic racism”. And honestly, there’re far too many white dudes speaking from places of unearned authority on the topic who get credence over Black, Asian, Latino and MENA folks are out doing the actual work. 

This is why the first thing I would suggest in terms of trying to make a difference in your community would be to seek out the people and organizations that are already in the mix. One of the most important questions someone can ask when they want to try to, say, push back against encroaching fascism and authoritarianism in their community, would be “Am I trying to recreate something that already exists?”, and then seek out the organizations that are already on the ground. Volunteering your time and effort with them is going to be far more effective than trying to duplicate the work of years from first principles, and doesn’t run the risk of confusing people, diluting available resources or otherwise butting heads.

This works on the micro level as well as the macro; there are resources out there already for helping correct mistaken beliefs about race, culture and religion and having those frequently awkward conversations with folks who may mean well but don’t realize why what they said is a problem. It’s much easier and less taxing when you can lay a little groundwork and then point them in the right direction instead of having to craft an entire educational framework yourself. Looking to these guides and resources can also help give you tools to avoid and minimize the pushback and defensiveness that can come up during these conversations.

There’re quite a lot of excellent resources to help guide these conversations, and I’d recommend Ijeoma Oluo’s “So You Want To Talk About Race” and Ibram X. Kendi’s “How To Be Antiracist” as starting points, as well as “White Fragility: Why It’s So Hard For White People To Talk About Racism” by Robin DiAngelo as starting points.

The second thing I would suggest specifically with regards to your family is to ask yourself which battles need to be fought, and which will just drain you of time and energy? As much as people’s misuse of the Paretti Principle is a continual pet peeve of mine, you don’t want to spend time on the 80% that gets only 20% of the effective and meaningful change.

Your dad is a prime example. As you say, trying to change him seems like something of a lost cause, but I think racism in this case is a lower tier concern than the abuse he’s perpetuating. His racism may be part of why he sees fit to treat you this way, but it’s also a tool he wields to hurt and isolate you and your mother. Whether he personally believes in the Orientalist tropes or racist s--t he spreads is almost secondary to the fact that he knows that other people are more likely to believe it and use that as the foundation for a permission structure to dismiss your complaints or concerns. If he didn’t think racist bulls--t would work, he’d use a different tool to achieve the same goals. You are right: changing his mind isn’t the point; blunting his ability to cause you harm is.

This is where talking to your family on his side comes into play, and where the resources I mentioned are useful. Even the most well-intentioned and progressive people can have blind spots – often areas where they never had to question their beliefs or learned that what they’re saying is ignorant or problematic. This is especially true if they don’t have much contact with many people of different races, nationalities, cultures or religions. Many times, they’re working from a lifetime of education and experience that prioritized a very narrow and colonialist narrative and haven’t been exposed to counter-examples that might have broadened their understanding.

They’re often looking at things through a particular lens, never realizing just how much that lens distorts what they’re seeing. It’s akin to Christians not realizing that other religions (especially non-Abrahamic ones) aren’t just Christianity with different overlays; they don’t know what they don’t know… yet.

There’s also a question of what needs to be addressed and in what order, especially if they don’t know they’re coming from a place of ignorance. Comments like whether your skin tone and appearance would grant you some protection from ICE is a prime example. While the issue of colorism is very real and their bringing it up (and reinforcing it) is problematic, that seems almost secondary or tertiary to my (again, very white) mind. It seems pretty clear to me that they don’t realize the underlying meaning of what they said – that you seem “white” enough to be safe from getting snatched off the streets by roving gangs of armed thugs and disappeared into another state without even a hint of due process.

It’s the default equating of “American citizen” with “white” – if not in skin tone and facial features, then at least in cultural assimilation and presentation – that enables so much of ICE and CBP’s acts of terror. Trump and Stephen Miller are relying on people tacitly accepting that non-white people aren’t “true” Americans and thus at the very least staying out of the fight. It also relies on the idea that people won’t care, beyond the abstract, until it directly affects them. That’s part of why it took the death of two white people in Minneapolis to get a lot of folks off the bench and into the streets to resist ICE: suddenly, they could see themselves as being under threat.

And, credit where credit is reluctantly due – the Trump administration isn’t incorrect about that. A lot of white people, even well-meaning progressives, are less likely to see the seriousness of what’s going on until they feel like it’s touched them and forced them to reexamine their beliefs and assumptions. If your father’s side of the family hasn’t had reason to have that unconscious equation of “US citizen = white = safe” challenged, they may not even realize they’re holding it in the first place.

Now, that doesn’t excuse things or make it better. While Hanlon’s Razor (“Never attribute to malice what can be equally attributed to ignorance”) is helpful here, there comes a point where ignorance and stupidity is functionally identical to malice. But if it is a case of – as the wise man said – “they’re a little confused but they got the spirit,” the odds are better that they’ll take correction and education as it’s intended.

This is why these discussions can end up being a matter of triage – determining what need is more dire and needs to be addressed first. Sometimes you need to make sure the patient isn’t going to bleed out before you address their concussion. Getting someone to realize that there is no “magic shield” that prevents ICE from kidnapping people they care about off the street – not proximity to whiteness, not being “one of the good ones”, their position in the community or even being a legal US citizen – is a strong starting point towards turning someone from inaction to positive action. When they can see someone they care about – you – as being under direct threat, they’re much more likely to be proactive in pushing back against the forces of authoritarianism than they might be if the threat were still abstract and “avoidable” or “preventable”. Realizing that the “rules” that would supposedly protect people are little more than magical thinking can be precisely what turns someone from a bystander to an ally.

It can also be the start of a better understanding of the ways race affects their perception. Realizing that they have had this particular bias lurking in the background is often a starting point for realizing that there are other biases, beliefs and assumptions that they may not have realized they had or understood to be racist. It can be the first crack in a wall of ignorance, and help them be more receptive to learning with less risk of knee-jerk defensiveness and ego-protection.

And to be clear: there is a lot of knee-jerk defensiveness to be had. I know people joke about how folks think being called racist is worse than being racist, but there’s a lot of truth to it. People don’t like seeing themselves as being “bad”, nor do they like having their identity challenged. Threats to that identity, especially ones that challenge one seeing oneself as “good”, can cause folks to dig in and choose to die on astoundingly stupid hills. This is why books like White Fragility can be helpful – it helps map out the location and origin of those defensive triggers.

As a general rule, if you want to have the most impact when discussing these issues, I’d recommend a couple tactics. The first is to have a firm grasp on the outcome you’re looking for, so you can shape the discussion in a way that will be helpful. It can be hard to keep conversations like this on track, because it’s a topic that’s prone to getting heated. Having a specific goal helps keep you focused on what you’re trying to achieve. Are you trying to dispel a stereotype or address a comment? Are you hoping to get them to recognize when they’ve said something ignorant, or change their behavior? Are you trying to debunk a myth or explain why what they said was a slur? Knowing where you want the conversation to go makes it a lot easier to direct things in a productive direction. 

Next, build rapport with them in ways that encourage them to see the two of you as being similar, especially in ways that are complimentary. Reinforcing that you’re both reasonable and intelligent people, for example, flatters them but also frames the discussion you have as being between two reasonable equals, rather than as someone getting a lecture. Emphasizing similarities and commonalities also breaks through a lot of “othering”; the more we see ourselves in another person, the more we identify with them and see them as being like us.

It’s also helpful to find areas where you can agree with them. This ties into that building rapport – you’re not saying they’re an awful person, you’re saying “we agree on a lot of the important stuff, we are just discussing this specific issue”, which cuts down on a lot of knee-jerk defensiveness.  

Seeking those commonalities also allows for what’s known as a “yes” ladder – the more you get someone to agree with you, the more likely they are to keep agreeing with you. By getting them to agree to “we” and “us” statements – “we both want X, neither of us want Y, we all prefer Z, people like us would say AB, yeah?”, you’re not just framing the two of you as being similar but subtly encouraging them to keep listening when emphasizing differences might make them shut down.

If you can, it’s a good idea to illustrate your discussion with a narrative, especially if you can explain how it affects you, personally. Stories are powerful tools in and of themselves. A story about someone they know amplifies that power, because it taps into the “here’s how this touches your life” that I mentioned earlier. A story about how X affected you is more powerful than an abstract, theoretical example. It also puts a face and identity on the effects of the behavior you’re trying to change; since your family loves and cares for you, seeing how things hurt you hits different than a stranger. But don’t hesitate to bring up stories in the news, especially if they’re recent – that can also make things seem less theoretical and more “real”.

This is a lot of work and the emotional labor of it all can be exhausting. It’s definitely work that takes time, rather than being a one-and-done conversation. But while these can seem small, almost pointless in the grand scheme of things… huge changes are made of small discussions like these. One small pebble doesn’t seem like a lot… but that one pebble can be the start of an avalanche.

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 (35f) have a friend (28m) who became my best friend and we got so close and there is this amazing connection for me even though he is married and I had been in a relationship for 19 years. However, we crossed a line and I don’t know how to get over him. We were planning an us and being together. I feel like I gave up everything for him but in the end, it feels like I was just used by my best friend. I wanna get over him because he means so much to me and is so important but idk how to.

Where Do I Go From Here?

DEAR WHERE DO I GO FROM HERE: This is one of those times where I wish you had included more detail, WDIGFH, because this is a case where details make a pretty big difference. It seems pretty clear that this was a friendship that became more… but how it crossed the line and why you feel used really affect what your next steps should be.

Now I realize that your letter doesn’t give us much in terms of your specific situation to work with. But there’re aspects that are pretty universal – feeling lost, like you’ve made a mistake, and wondering just how you can move forward and what you’re going to have to do if you want to have any hope of salvaging one or all of these relationships… or if that’s even possible.

So, without trying to fill in too many gaps with speculation instead of facts, here’s what I will suggest.

Start with taking stock of your feelings. Yes, you feel hurt and lost, and it seems pretty clear that you feel like you made sacrifices that weren’t appreciated or reciprocated. But can you put your finger on the particular whys and what of how you feel – the precise shape and texture of these feelings? Do you feel, for example, that you were deliberately mislead, or do you feel like you let yourself get out over your skis? Are you feeling betrayed – that he did you wrong – or are you feeling foolish – that you should have known better? Do you feel like you saw things that weren’t there, or do you feel like he took advantage of your relationship and exploited it? Or maybe it’s a bit of both; you’re feeling like you were tricked and you should have caught that he was trying to trick you?

Similarly, does this feel like a sudden surprise, or something that was both long-in-coming and possibly inevitable? Does it feel like something neither of you could have accounted for, or was it a deliberate rug-pull? Does it feel like they were never going to go through with any of the promises they made, or that someone backed down or away at the last second? Do you feel that your friend was saying what you wanted to hear just so he could get whatever it was he wanted, or does it feel like he was sincere, but then everything fell apart? Does it feel like someone changed their mind, were incentivized to do so, or perhaps that there was an imbalance in feeling somewhere along the way?

I realize these all sound like distinctions without a difference, but getting a better sense of precisely what you’re feeling and why is incredibly helpful, because it shapes what you’re going to need to move forward. A big part of redemption, closure and making amends means understanding and recognizing what you’re seeking these things for.

If you feel like you had been led on and betrayed by someone who simply sought to use you, then part of the answer to how to move on is to understand how you were misled, so you can recognize why it worked and not get fooled in the future. If, on the other hand, you feel like this was you falling harder for someone than they fell for you, then you can have greater clarity in hindsight about the signs you missed and how to avoid making the same mistakes in the future. If you feel like you were an equal party in how things went down, knowing the four corners of your involvement is going to be important for how you may seek to make amends or what you’re asking forgiveness for and why. It also will make a big difference in what sort of relationship you’re going to have with your friend going forward, if any, and under what circumstances.

It also helps to see what other factors lead to the fateful choices that brought you here. Were you feeling something for your friend that was lacking in your relationship? Was there a need that was going unmet that this friendship was filling? Was it a matter of reciprocation – the way he behaved made you feel a particular way, so you were grooving on what his feelings were bringing out in you? Was the thrill of this relationship intoxicating to the point that you ended up throwing caution to the wind?

Here’s the thing: what’s done is done and it can’t be undone. Time only moves in one direction and we have to move with it. You can’t make whatever happened unhappen. The most you can do is understand it, recognize your part in it and try to learn from it so that you don’t repeat this in the future. Taking responsibility and owning your actions is going to be important. Making sure that you’re only taking responsibility for your actions is important too; it’s easy to feel like you are guilty for things that weren’t actually on you, especially if you were manipulated or mislead by someone who wasn’t acting in good faith. It doesn’t do any good to take on guilt that’s just being offloaded by someone else who doesn’t want to own his side of things.

So, make sure you’re firm on what you’re feeling and why. Do your best to understand how you got here, why you made these decisions and why this was a mistake. Do your best to be clear on what is on you and what is on them. Apologize where you can, with the understanding that the people you hurt may not accept your apology and are under no obligation to do so. Make amends where you can and be mindful of where trying to do so might cause more harm than good. Be conscious of how this happened so that you can resolve not to make these mistakes in the future.

And do your best to forgive yourself. As much as you may want to kick your own ass or however much you feel you f--ked up, part of moving on is being willing to forgive yourself so that you can do better in the future. Even if the thing you need to forgive yourself for is ultimately loving not wisely but too well.    

Good luck.

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