My girlfriend says she absolutely hates Valentine’s Day and doesn’t want to celebrate, but it’s one of my favorite holidays. How should I go around her anger towards the holiday so I can still enjoy it myself? -I Love Love Dear I Love Love, I cannot express to you how much I personally belie… READ MORE

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All of these people are sending you dating questions and I’ve come to realize I’m going to die alone. -Sad, Annoyed and Allergic to Cats   Dear Sad, Annoyed and Allergic to Cats,   This column may be the most honest thing that I’ve written, and while I probably should be sorry for pretending to […] READ MORE

My boyfriend really likes to talk about his past relationships whenever we’re together and compare me to them. One of his favorite phrases is, “You’re not like anyone I’ve ever dated before.” I’ve asked him to stop before, but he still talks about all of the other girls. Is there anything I can do without […] READ MORE

I tell my girlfriend I love her a lot and am constantly trying to show my affection, but I generally get nothing in response, but a smile or she tells me to shut up? Should I stop? -Affectionate   Dear Affectionate,   You seem to have found yourself a wise girl. Congrats! From what I […] READ MORE

I was sexting a girl from Tinder on Snapchat the other week, and I thought we were having fun, but after we were done she blocked me on everything. Turns out we have a lot of the same friends, and now I see her a lot. Should I call her out? -Can’t Ghost Me Now […] READ MORE

How do you break the ice with a girl? -Horny and Confused What’s up Horny and Confused, First off, I’d like to commend you for putting your judicial aspirations on hold in favor of bothering to break the ice. This is a pretty hard and fast way to both minimize suffering and hassle for both […] READ MORE

I’m just out of a serious long term relationship as of August and have already started seeing another guy. Is it too soon to move on? -Sincerely, Confused The best way to gauge whether this is too soon is to see if you have any reasons to feel guilty, but there is no reason to […] READ MORE

My boyfriend keeps talking to me about what he wants to do to me, but hasn’t gone for more than a kiss. Is he for real or just playing me? I want to know if I need to make the first move or not. -Daring Dreams Dear Daring Dreams, Sexual chemistry is one of the […] READ MORE

My boyfriend and I have been dating for almost six months and I thought that we’d both agreed that we don’t want kids. But while he was drunk, he admitted that he does want them. -Sincerely, Still Don’t Want Kids Dear Still Don’t Want Kids, Having kids is a mortifying double-whammy of both moral considerations […] READ MORE

How do you date in the age of technology? What’s the possibility of finding someone when most of our interactions are online/through text? Sincerely, Tech Savvy Dear Tech Savvy, Like most of life, dating is relegated to digital representation in lieu of anything that could be principly described as real. Since there are so many […] READ MORE

What should one do when the girl that they like doesn’t respond to their messages? Sincerely, Ignored Dear Ignored, While the Western world’s general fascination with instant gratification and easy access to information can be frustrating, it has the happy side effect of making simple relationship calculus considerably less painstaking. At least in the United […] READ MORE

“I have an ex who is really sweet, and I care about their feelings a great deal. I can’t seem to get them to understand the space that I need post-relationship. How do I get my point across without being hurtful or too blunt?” -Sincerely, Claustrophobic Dear Claustrophobic, Breakups are the fine print that people […] READ MORE

Dearest Caleb of the Meet Market, You may have remembered me from my last letter I wrote to you about a difficulty with asking to partake in an evening with my co-worker. There is currently another fair maiden in my English class that I’m also quite fond of. We have participated in evenings of indulgence […] READ MORE

“Should I go to my girlfriend’s house for spring break? We’ve been dating for a year and a half and I don’t know if I should.” -Decrepit Invalid Dear Decrepit Invalid, Spring break is often considered to be the most fun time during the semester, which is because it is the least painful series of […] READ MORE

So I asked a long-time friend on a date recently who said yes. We have a long history of back and forth flirtation. However, recently he has been not treating me very well. My friends say he’s no good for me but I still find myself going back and forth. Should I go on the […] READ MORE

“My girlfriend says I’m not hip and cool. I don’t have the newest emojis and my favorite movie is the Big Lebowski. Should I dump her for not being as cool as me, or should I dump her because we don’t mesh well? I want to be as delicate about this as possible. -Good Guy” […] READ MORE

“What do you do when you’re in love with someone who doesn’t love you back?” -Swetea23 Dear Swetea23, You should view your relationship as the one-sided affair that it is. You should stay as long as it continues to have use to you. Think of your person as a sort of emotional ATM. Keep withdrawing […] READ MORE

Dear __ I’m newly single and still recovering from a toxic relationship. I’m worried my past experiences will keep me from fully putting myself out there again and being really open with someone. How do you stay cautious so you don’t rush into anything, but open enough to be able to find something potentially great? Sincerely, […] READ MORE