Never Upgrade A First Date

Photos courtesy of @alittlenudge Okay. Let's unpack this. Who pays on a first date etiquette dictates that the person who asks, should pay. That's reasonable. The rules are the same for who pays on a coffee date, too. In fact, who pays on a date really should only be a question for the first date. After that, there should be no confusion: split everything 50/50. Ideally, you want that to be for all dates, even the first ones, but I digress. (Reddit dating advice subs are great resources for first date tips, btw.) In this scenario, the woman - despite not being attracted to the man - still expected him to offer to buy her a meal. To be fair, she's clearly over 60 at the very least. People in

Social Distance Dating Tips

I was messaging with a guy from I asked him if he wanted to do a video chat later that afternoon or the next day. Crickets. Should I suggest a phone call instead? Ugh. No. No phone calls. Phone calls are The Worst. Most people suck at making small talk. Plus, taking on the phone nowadays is usually reserved for family, close friends and work obligations, That's it. People don't even use voice mail anymore. A lot of people feel uneasy doing video chats from their home. They might feel embarrassed that they live in a small place or feel their home is disorganized and not clean enough. Others fear they will be rejected in person, an understandable concern. Mostly, though, the people

Why Pronouns Matter

Slowly, mainstream dating sites - both free and paid dating sites - are updating their basic details sections so that users can specify their preferred pronouns. One of the reasons I'm a fan-ish of OKCupid is because they're the only mainstream site that has integrated gender identity, trans rights and equality into their dating profile template. Much like my previous post about racial preferences, I'm going to urge all dating app and dating site users to update their profiles where possible and include your chosen pronouns ie he/him, she/her, they/them etc. In fact, I would encourage anybody reading this to update all of their social media bios to include this information. There are multipl

Delete These Lines From Your Dating Profile ASAP!

Since a big chunk of my job involves giving dating advice and reviewing people dating profiles, I thought I'd put together a little crib sheet of common phrases you might see in someone's bio. (Extra bonus: avoid these really bad pick-up lines.) NOTE: In cases where I provide a breakdown for men and women, I'm referring to cis straight people only. The rest are all-inclusive. WHAT THEY SAY: I'm looking for someone fit TRANSLATION: I'm looking for someone conventionally slender or lean. WHAT THEY SAY; I'm looking for someone who takes care of themselves TRANSLATION: I'm looking for someone who has managed to stop the aging process completely and is as active and vibrant as I think I am. WHA

How Come She Never Meets Available Men?

How come I only seem to get approached by either physically or emotionally unavailable men?  The only 3 types that ever seem interested (in person or online) are 1. in a relationship, 2. looking for someone temporarily before their next relationship, or 3. players looking for a buffet of girls to choose from. The operative word here is "seem." You "seem" to exclusively attract unavailable men. Only in the case of men in relationships can you be sure they're unavailable. As far as the other two categories, it sounds like you're making assumptions based on behavior you perceive as inappropriate or unavailable. You're not in the heads of these men. You don't know what is motivating them.

When Is It Okay To Talk Money?

What do you make of someone revealing their financial problems after only a couple of dates? In general, talking finances that early on in a relationship is unwise. The reason is that most people (incorrectly) equate financial instability with irresponsibility. It's great that your debt is low and your credit is high. It's fantastic, in fact. However, if you're single with no dependents, no divorce, and no health problems, your situation is not comparative to someone who has or currently is struggling with those issues. It's very easy to have low to no debt is you didn't go to law or medical school, don't have child support to pay, get laid off from your job, etc. The first thing I want to

The Problem With "Preferences" In Your Dating Profile

One of the things I am most grateful for during my time writing And That's Why You're Single is proverbial mirror certain readers would hold up to my face from time to time. I was fortunate to have black people in my readership - Craig, Jaimie, Heather - who thought enough of me to take the time and perform the emotional labor to point out my blindspots when it came to race. It's with that in mind - given this seismic societal shift we are hopefully experiencing - I felt compelled to raise the topic of race, preferences and online dating. I perform about eight to ten dating profile reviews a week. Something I see more often than I'm comfortable with is Caucasian people selecting either "Whi

How To Make Dating Apps Suck Less

In a recent online discussion group I moderated, someone asked, "Once you match with someone, how do you keep the conversation from fizzling out?" Picture, if you will, Jeremy Renner as an IED (improvised explosive device) specialist in The Hurt Locker. He's all suited up and trying oh-so-delicately to diffuse a bomb. Which wire does he clip? What if he cuts the wrong one?? EVERYBODY IN A FIVE MILE RADIUS COULD DIE!!!!! Writing messages is kind of like that. There's a delicate balance required; you don't want to seem too invested nor do you wish to seem aloof. Respond too quickly and you look desperate. Take too long to answer and you could get unmatched. That intro message sets the tone f

The Other Woman Is Not To Blame Because Your Man Sucks

Medium continues to serve up essays reeking of internalized misogyny with this latest pile of word vomit. Who is the Other Woman? I have a friend who repeats the same pattern in every relationship. Let’s call her Bertha. Bertha has never, in twenty years, pursued a man who is not married. Twenty years of furtive exchanges, clandestine meetings, and stolen time. Just so we're clear: Bertha doesn't exist. How do I know that? Because the author wouldn't have the balls to write this essay knowing Bertha could read it. In the off chance Bertha is real, the author is a passive aggressive bitch and really had no business writing scathing take-downs of other women when she clearly sucks hard at b

How Do You Get Matches To Meet Offline?

From last week's Ask & Answer online session - (Attend the next one - RSVP here) I get matches on Tinder and Coffee Meets Bagel but all people want to do is message. How do I get people to meet me IRL? This one is simple: ask them. Rather than focus on who asks whom, seize the moment and suggest a video-chat. For the past three months, people have had time to familiarize themselves with Zoom, Google Hangouts, etc. A video chat is low-stakes enough that most people won't feel as pressured to take things to the next level. When you first begin to message, don't use that time to ask interview-style questions. Use something in their bio or profile as a springboard for light conversation. Do they

What Does "Intimidating" Really Mean?

What does he mean? I recently had a video date with a man I met on Bumble. After we chatted, he sent me a message saying he enjoyed speaking but didn't think we were a good fit. I thanked him for his honest but expressed confusion. I thought the conversation had gone well. He further explained that he found me intimidating. I asked what he meant but he didn't respond. The next day he unmatched me. WTF? As difficult as it is to hear something like that, I'm going to implore you not ignore his comments or write-them off as a man being insecure. Yes, that's totally possible, but it's just as likely he's using the word intimidating as a catch-all phrase in place of descriptors like unpleasant or

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