The New Rules of Dating in Philly

The hunt for love in the age of Bumble, Trump, sexting and #metoo.

Adam Reed and Melissa Gee, Charlie Was a Sinner, 1/6/18. Dating: 6 months. The connection: Met at work. Photography by Nell Hoving

A while back, on a Saturday afternoon, a couple of girlfriends and I were lounging at a house in Fishtown, chatting about life over glasses of chardonnay. We got to discussing first dates, particularly how the bill should be handled when the night’s coming to a close. We’re all mid-20-something women living in Philadelphia, and yet we were all over the map. One friend said she certainly passed judgment if a guy didn’t pony up on the first date — surely there are men out there who are feminists but still want to wine and dine a girl. Be a man and pay for my dinner! she declared. Another mentioned that she wouldn’t dock points, exactly, but definitely appreciated it when a guy picked up the tab — I mean, we do work in creative industries, she noted. Another argued that expecting a man to cover the bill (and consequently judging him if he didn’t) was transactional and archaic. We agreed to disagree and sipped our wine.

I’m guessing we’re not the only ones who can’t seem to find unanimity when it comes to best practices in courtship these days. Even though we’ve got tech aimed at making it easier than ever to find the perfect Philadelphian (a 97 percent match!), our rapidly evolving social norms, changing expectations, and unprecedented connectedness mean concrete rules of dating are as elusive as ever. So how does one nimbly navigate finding The One in 2018? I asked some Philadelphians on the dating scene to lay out their most vexing questions — and savviest answers.

Success on dating apps is all about first impressions. What rules can I follow to make myself stand out?

“It’s based off of looks, but also if someone has a witty caption,” says Bernard Bennett-Green, a 25-year-old project manager at CBS who’s from Cheltenham. “Humor is a big thing.” When you message someone new, keep it light, but be creative — a remark about someone’s bio usually sparks some intrigue. According to a lot of men and women, sending a simple “hey” is plain boring and relays the wrong message — that you’re just like the 16 other “heys” among their DMs who couldn’t muster up anything more interesting to say. All-too-specific compliments, or sexual remarks right off the bat? Keep them to yourself.

And, of course, nailing your profile imagery is crucial. For starters, post pictures that have good image quality (common sense) and that actually look like you (people will notice one too many filters). Second, pick a readily identifiable photo. Nobody wants to play detective to uncover which of the seven people posing at the Eagles game is you. Plus, according to a couple of guys I talked to, if your friends are hotter than you, you’re not doing yourself any favors. Another thing: Don’t post a photo of you holding a baby unless it’s your baby. (Some men seem to think posting pictures with a baby has some sort of subliminal psychological effect on potential matches, but it just confuses everyone swiping through.)

According to Aziz Ansari’s best-seller Modern Romance, data from OkCupid shows the most effective profile photos for men and women differ a lot. For women, selfies where you’re “flirting to the camera” have a greater response rate than just your average “straightforward smiling pic.” For men, oddly, a photo of a (not smiling) guy glancing off into the distance does the best. Philadelphians told me that travel photos or pics that show off a hobby you enjoy are always crowd-pleasers, too. One last takeaway: We all know everyone’s got a past, but don’t post a photo with your ex and scribble all over his face. It’s just weird.

How do I choose the dating app that’s best for me?

Knowing which app is right is all about knowing the audience. So do a little research.

“Tinder is just, like, a meat market,” says 28-year-old Mark Kuhn, CEO of Philadelphia-based artisanal builder Oat Foundry. If you’re looking for something casual, playing the numbers game on Tinder or Grindr or Bumble is a surefire way to a quick fling. And while actually dating on those apps is doable, you’ll have to wade through a lot of noise to find the gems. That said, Matt Hotz, 42, a business analyst from East Passyunk, says dating on Tinder does make things more efficient: “If you meet somebody at a bar or a party, you don’t have their answers to 50 questions and a résumé and a carefully curated profile.”

Other apps dig a little deeper and prioritize more serious inquiries: “I’m a big fan of The League,” says Michael Scarpati, a 30-year-old financial planner from Grad Hospital. “Tinder’s the volume game — you’re not thinking; you’re just swiping left or right. The thing about The League is, it gives you two to three people to match with per day. You only get three, so there’s a little more due diligence.” Emily (her name’s been changed), a 27-year-old from West Philly who works in education, says that on OkCupid, particularly in the queer community, users seek a wider variety of relationships, ranging from friendship to monogamy to polyamory. People’s intentions on dating apps vary drastically, and finding what you’re looking for means choosing a platform that mirrors your expectations. And if you can’t seem to find the right mate online, don’t rule out serendipity just yet.

Should I take down photos with my ex from social media?

If people scroll down a little on Facebook and up pops you and your ex kissing in front of the LOVE statue, sure, go ahead and hit delete on that one. People understand, though, that it’s almost impossible now to completely erase a relationship on social media unless you spend a day digitally cleaning house. And doing so might even raise a red flag. Becca Cohen, a 28-year-old full-time student at Drexel who lives in Fairmount, says she wouldn’t expect someone she was seeing to take down photos from a past relationship: “I think it’s pretty when people leave up memories. It’s a part of my life. I’m not going to force myself to erase it. And I want you to have it up; that was a part of your life.” Bottom line: Trash anything with blatant PDA; leave whatever else.

Left: Kimberly Nolan and Sean Leary, Winterfest, 1/5/18. Dating: 2 weeks. The connection: Friends since high school. Right: Madelyn Staley and Kris Lee, Gleaner’s Café, 1/13/18. Dating: 2 years. The connection: Both UArts dance majors.

Post-2016, are politics something to be up-front about on a first date?

Previously a taboo topic of conversation, your political leanings have been elevated to must-know, potential-deal-breaker status in a post-2016 climate. For many of us, political choices speak to a person’s values and should be discussed early on in a relationship’s life span. “I think the idea that there’s this separation between personal life and political affairs is a bogus distinction,” says Margaret Smith, 45, a high-school teacher from South Philly. A lot of Philadelphians I spoke to say they’re definitely curious about a date’s political affiliations (an I-would-never-date-a-Trump-voter sentiment was frequently expressed), but that they generally assume they’re breaking bread with someone whose views are on the same side of the political spectrum, especially given Philly’s left-leaning tendencies. (Friends of mine describe relief when politics do enter the conversation on a first date and their assumptions are confirmed.)

For others, though, politics and the like are still taboo subjects that don’t have a place on the first or second date but should be revealed over time. “I don’t think that’s first-date stuff,” says Michael Scarpati. “I’m a pretty open-minded person, so I don’t really care. Just because somebody voted for someone else doesn’t make them a terrible person. Like, we’re all of a sudden going to cut the pool in half because of that? That’s silly.”

If you need to know how someone leans politically, the best way to find out is to just ease it into the conversation — throw in a light joke or an unassuming comment. Your date will get the hint, and the response will let you in on where he or she stands. Here’s hoping things don’t get too heated over the first round.

Is there a wait-three-days-to-call rule anymore? What about texting?

Most people follow up via text now, but there’s no one-size-fits-all rule about how soon is too soon. If you want to ask someone out, don’t feel like you have to wait a significant amount of time. Though some people opt to wait a few days to reach back out, many like the honesty of texting right away — it points to confidence and says you’re not afraid to show someone you’re actually interested. And don’t think picking up the phone and dialing someone’s number is necessarily too much, either. If you’ve already met in person and you’re confident in the connection, the extra effort can feel novel and sweet.

Left: Hailey Brinnel and Nick Lombardelli, South Bowl, 1/8/18. Dating: 4 months. The connection: Both trombonists. Right: Joshua Walker and Eshea McElvy, Winterfest, 1/6/18. Dating: Nearly 3 years. The connection: Met online.

A lot of guys are annoyed by “the reach.” What are the for-real expectations after the check hits the table?

When the bill comes around on a first date these days, all bets are off. Guys say many times, they feel like they’re going to fail a covert litmus test if they don’t immediately offer to cover the tab when their date reaches for her wallet. Many of the women I spoke to for this story confirm that instinct — even though they often offer to split things 50/50 on a first meeting. If their date takes them up on that … well, then they’re not so sure.

But some women are truly happy to split the bill to avoid unwelcome expectations, or simply because they had a good time. “Sometimes I’ll just take the bill, and I don’t think it’s something they expect,” says Janelle Ortiz, 31, a nursing student. “But it’s touchy, because some guys get offended by it.” That said, there are men who aren’t so traditional anymore: “If you’re out on a date with someone and you’re like, ‘Hey, I’m having a good time. I want to pay for the drinks,’ and I’m like, ‘No no no, the man should pay’ … well, that’s bullshit,” says Mark Kuhn. Matt Hotz says if there isn’t too much chemistry between him and a date, women are more likely to want to split the bill — and he won’t put up much of a fight to pay or pursue things further. “I understand there are fairly complicated cross-gender power dynamics there. … If it was pretty obvious there wasn’t going to be a second date, I didn’t want the woman to feel like, ‘Why isn’t this guy picking up the signal?’ or feel reluctant.”

Beth Orr, 50, says when she started dating again post-divorce, she was surprised to see how the bill-paying protocol had changed, but that splitting makes sense: “I just assumed the men would pay, because, you know, that’s how it was. I was dating someone for a while and I thought, why is he always paying? Is that really fair?”

Rule of thumb: Be real about what you expect, and try to accommodate the other person’s wishes. Don’t offer to split if you don’t mean it, and don’t insist on paying if a date insists on splitting.

People are going on a ton of dates now. What are the sexpectations?

Despite all the instant gratification of the Tinder age and a dating scene with a reputation for “hookup culture,” most single Philadelphians indicate they’d prefer to hold off on sex for a little while. (It’s not necessarily surprising: A 2016 study from the journal Archives of Sexual Behavior found that millennials, overall, have fewer sexual partners than both Gen Xers and boomers.) That’s not to say people don’t admit to having had one-night stands on occasion, but generally speaking, having sex on a first date isn’t what people are expecting to get out of the night. (A lot of people say that having sex on the first date means they probably don’t see the relationship going much further.) After a couple of dates, though — the third date seems to be a milestone and ups the anticipation of a sleepover — sex is expected to be a part of figuring out whether there’s real chemistry or not.

How soon is too soon to start sexting?

That depends on … a lot of things. Some women say they won’t sext with someone until they’re in a committed relationship, if ever. But one friend I interviewed says she’s sexted with people she’s matched with on Tinder before they even met up.

It’s safe to say that for most people, sexting is something they prefer to have go down later rather than sooner, so be sure not to jump the gun. More specifically: Sending naked pics of yourself to initiate sexting is definitely not the way to go. Be sure you clearly understand someone’s boundaries before you go there.

Rajvir Jutla and Mimi Jeon, 17th and Addison streets, 1/9/18. Dating: 9 months. The connection: Residency at Philadelphia VA Medical Center.

Is chivalry sweet or insulting? (Or just dead?)

“My mom raised me with chivalry in general — always open the door, walk on the outside of the road. Women are always fine with me doing that,” says Bernard Bennett-Green. Though a bunch of guys claim chivalry is still upheld as a value in the dating world, most women I spoke with insist it’s gone by the wayside. And they wish it would make a comeback. “It’s becoming a lost art,” says 30-year-old Shelley Dailey, from West Philly. Janelle Ortiz agrees. “Our grandparents, even our parents, they very much pursued the other person, and I just don’t think that’s the case anymore,” she says. “When, in my mind, it should continue throughout dating and into marriage. And women should do it, too.” If you’re holding doors or draping the coat over your date’s shoulders, it might earn you brownie points; short of that, though, common courtesy will get you by.

What’s the best way to tell someone you’re just not interested in them?

We’ve all been there: You’ve got a good text repartee going with someone for a few weeks, maybe you’ve been on a date or two, and suddenly … radio silence. Everyone I interviewed for this story admitted to having been ghosted before and to ghosting someone else. Interestingly, though, almost none of them approve of the harsh, cold-turkey method as a means to an end.

“It allows people to avoid awkward conversation — something that makes them uncomfortable. People don’t want to do things out of their comfort zone. And talking on the phone is out of most people’s comfort zones,” says Shelley Dailey. According to Modern Romance, one 2014 survey found that texting was the most popular way to break it off with someone among 18-to-30-year-old participants.

Telling someone you’re not interested in moving forward — whether via phone call or face-to-face — is the most uncomfortable route to go, bar none. But in the end, you’ll win points for consideration. Plus, if you run into the person later (which you will — this is Philly), you won’t have to duck out of the way because of embarrassment.

There are the #metoo and Time’s Up movements. The Silence Breakers were named Time’s Person of the Year. Is the increased conversation about sexual harassment and sexual assault going to change dating dynamics?

Short answer: Where needed, we hope so. Both men and women say they don’t see the current climate having any major chilling effect on casual dating norms, but they’re optimistic that the issue of consent will be taken more seriously in the future because of it. Shannon (her name’s been changed), a 26-year-old fund-raiser for the City of Philadelphia, says the cultural shift is empowering women: “I don’t think it’s changed the way men have pursued sex — there’s no point in the make-out session where they’re hitting me with a ‘Are you down for this?’ But I think women are now more vocal about what we want. And the culture is a little more comfortable with women saying no.”

Published as “The New Rules of Dating” in the February 2018 issue of Philadelphia magazine.