Dear Hipster: With the holidays upon us, I would like to know how a hipster would deck the halls. What type of gifts might be given? What food would be served? Do hipsters do holiday …

Dear Hipster: One thing this crappy year has got me thinking about is time travel. If time travel were indeed possible, we could go back in time and quarantine patient zero before the coronavirus pandemic, …

Dear Hipster: Since life is still canceled, I have been thinking about doing some kind of old-school Christmas festivities this year. Got any suggestions for how to make the most commercialized holiday season in the …

Dear Hipster: 2020 is almost over, and I think we can all agree it’s been a hell of a year. Rather than dwell on the weirdness of 2020, I want to take a look back …

Dear Hipster: I was reading your column from a few weeks ago where you talked about sitting around, drinking beers, and holding down heartfelt conversations about thirty-year-old alternative rock bands. To me, that sounds like …

Dear Hipster: I was talking to a coworker of mine the other day. You can safely assume he (or she) qualifies as a real hipster. I can’t remember exactly how we started talking about it, …

Dear Hipster: As the chill of autumn settles in around us, I think the most burning question on everybody’s mind is... sweater, hoodie, or jacket? Which method of fending off the cold reigns supreme? — …

Dear Hipster: What will be the top recreational drugs for hipsters in 2021? I’m guessing booze and buds, but not necessarily in that order, and I could be wrong. Anything else that may be on …

Dear Hipster: I have been contemplating a new car for a while now. Try as I might, I can’t find one that suits me. For starters, it is getting hard to find a ride with …

Dear Hipster: This was supposed to be the year for Halloween. Not only did the actual holiday fall on a Saturday, it was a full moon to boot! I mean, could you ask for a …

Dear Hipster: Was wondering where hipsters stood on the subject of God and religion. The other day, a dude I know took to Facebook to complain about how a plumber in his house went on …

Dear Hipster: Sorry in advance for the long-ish message here, but it actually takes some explaining to get my point across. Anyways, I was sitting around my house the other day, watching TV — wishing …

Dear Hipster: How are you qualified to be the authority on all things hipster? It’s not like one can go out and get a PhD in Hipsternomics from Stanford. Please don’t take this the wrong …

Dear Hipster: Is there a moment that you can identify as the birth of the modern hipster? — Dick, Bankers Hill Well, as I have said before, the hipster is eternal. There have always been …

Dear Hipster: As the hipster population ages, with older hipsters beginning to receive benefits such as social security, has hipster gentrification been creeping in; whereby the older, now more affluent hipsters upgrade their digs, further …

Dear Hipster: Would it be possible to ironically drive one of those mondo lifted brodozer trucks, or is that too on-the-nose for even the hispterest hipster? — Charlie I once had a hipster friend who …

Dear Hipster: I have been working in the service industry for several years, and I consider myself a consummate professional. Recently, some office-worker friends of mine and I were having a discussion about work, and …

Dear Hipster: What are some non-hipster things that are secretly (or not so secretly, considering you will publish this for all the world to read) revered and enjoyed by even the snootiest hipsters? — B. …

Dear Hipster: If aliens invaded the Earth tomorrow bent on our destruction, who would be the best person to act as a diplomat on behalf of the entire world? — Tycho, Hillcrest I’m weirdly flattered …

Dear Hipster: When are you going to cover that mugshot of yours in the Reader with a mask? You could just draw one on that supposed likeness of you. — Sam King, El Cajon You …

Dear Hipster: If a vampire ate too many hipsters, would it suffer any ill effects? — Chad If vampires were anything like normal humans, which they might well be if they existed, then they would …

Dear Hipster: Rose (rosé?) wine: hipster, trendy, or merely pretentious? — Kate There are exactly two mainstream wine drinking positions that account for something like 98 percent of the people you will find raising a …

Dear Hipster: Concerning your article about the North Star, the North Star is not exactly above our North Pole. It is about 1 degree off the true North Pole. You mention taking a time lapse …

Dear Hipster: Although I love dining out, I haven’t been to a restaurant since March. At first, everything was closed, and I spent all this time pondering when I would be able to go and …

For whatever reason, I receive a steady trickle of bizarrely ordinary inquiries. I suspect people fire them off for no other reason than that they can. How can something be “bizarrely ordinary,” you ask? Aren’t …

Dear Hipster: I’ll probably out myself as an aging hipster has-been here, but I have to ask: is there a word for the feeling you get when you hear kids talking about stuff that used …

Hey Hipster: Maybe I’m losing my mind because I’ve been locked out of my Amazon account for a week, and have thus been deprived of all the mindless streaming video entertainment that might distract my …

Dear Hipster: I was reading the twitface newsfeed nonsense about Elon Musk and Grimes naming their baby a string of alphanumeric characters. Now, I don’t really care one way or the other about celebrities vying …

Dear Hipster: Considering the ubiquity of pandemic-related news coverage, which has even started to infiltrate something as innocuous and not-particularly-newsworthy (no offense, obviously) as Ask a Hipster, I thought I might throw you a bone …

Dear Hipster: If I were to spend my quarantine trying to master an incredibly complicated game (you know, the kind of thing everybody always says it takes a lifetime to master), would it be cooler …

Dear Hipster: You may be too much of a young’un to remember the tribute album craze of the 1990s, which really extended well into the Aughts, but I sure do, and not altogether unfondly! Some …

Dear Hipster: The recent warmth and sunlight have rekindled the smoldering passion in my heart for my one true love: ice cream. I adore all the flavors, even the weird ones that maybe ought not …

Dear Hipster: I’m a hugger, not a hand shaker or a cheek-kisser. But I worry — is hugging dead forever, because everyone will be scared to touch each other for the foreseeable future? I actually …

Dear Hipster: You wrote recently about how it’s very hipster to be suspicious of anything that too many people like, and therefore definitely “not into” such popular things. People who enjoy logic might express this …

Caught between a hug and a hard place If you move to somewhere on the East Coast, such as Boston, NYC, or Philadelphia, fewer people will try to hug you, mostly because they’re all too …

Dear Hipster: I transplanted here a couple of years ago from Portland, Oregon, and I noticed that on average, hipsters in Portland are way meaner than those in San Diego. What gives? — Progressive Guru …

Dear Hipster: The more people tell me to watch Tiger King, the less I want to watch Tiger King. Am I being a total hipster because I refuse to watch Tiger King as my go-to …

Dear Hipster: As we all know, the coronavirus pandemic is nothing more than a consolidated effort by home delivery grocery apps and Netflix to keep us permanently combined in our homes. It’s actually sort of …

Dear Hipster: I think it is patently unfair for you to invoke the quasi-divine, vaguely porklike glory of the McRib during these trying times. Did you not think we had it bad enough being forced …

Dear Hipster: I hate to dwell on it, because it seems like it’s all anybody can talk about lately, but every answer I get on this whole “social distancing” thing raises ten more questions. Should …

Stop the presses! Pump the brakes! No diving straight into questions this week, people. I don’t know if you heard, but there is this thing called a “coronavirus,” which is apparently a super big deal. …

North Park and South Park – say goodbye to 30th Street as it is The main roadway connecting North and South Park may be on the eve of a massive transformation. Councilmember Chris Ward is …

Dear Hipster: Is it possible to predict what current pop culture trends will someday be the target of a revival, either ironic or genuine? Perhaps history suggests a pattern as to what captures future imaginations, …

Dear Hipster: I was going through some things in the garage the other day, and I came across my old VHS collection. I tell you what, Mr. Hipster, there were some serious gems in there. …

Dear Hipster: Please help me with something that has been puzzling me of late. I think we can agree the whole “retro stuff is super hipster” thing is established beyond dispute. Nevertheless, I have noticed …

Dear Hipster: Here is a puzzler for you. I always hear about hipsters being super socially conscious of all the world’s ills, and letting this concern guide their decision-making towards (mostly commercial) activities like drinking …

Dear Hipster: One minute all the cool kids are dopamine fasting, the next minute everybody’s like “OK, Boomer,” and before you know it they’re dreaming up epic power metal covers of the “Toss a Coin” …

Dear Hipster: I often hear people talking about hipsters and Millennials as if the two are coextensive. Other times, people equate hipsters and Gen X’ers. Sometimes Generation Z takes the blame (or gets the credit, …

Hipster: I’m growing older. I found myself scoping out even more suburban places recently. Though I seek peace and tranquility, maybe I can’t do it. Just too far from the hip. I guess La Mesa …

Dear Hipster: What were the best and worst parts of 2019? — Zadie From the hipster perspective, the best part of 2019 would have to be the brief return to popularity of the scrunchie. Ordinarily, …