Let’s face it: dating is rough. A first date is almost always stressful. It’s always nerve wracking to meet someone new in the hopes that the spark will be there, you have something in common, and romance will blossom. In some ways, it’s even worse for us guys.

Men are expected to ignore all their insecurities and be bold on a first date, to hold the doors and of course pay for drinks. At the end of the night, it’s often up to us to decode a woman’s signals and make (or not make) the right move.

The major problem with online dating, however, is that no matter how great a woman seems on her profile, she could turn out to be completely different in person. She might crack you up on Whatsapp with this adorable sense of humor, but when you meet for the first date, there’s just no chemistry and no laughs. Or maybe she just brings with her an insurmountable amount of baggage and hang-ups.

Whether you go the mainstream route with Match, Tinder, or Plentyoffish, or try to stack the deck by signing up for JDate, Stoic Matchmaker, or Farmers Only, online dating can be fraught with pitfalls. Today we’re looking at the various personality types you might encounter on a first date.

Obsessed-with-Her-Ex Olivia


Sure, at some point during the first few weeks of dating, you’re probably going to talk about the ex. You’re going to give each other a rundown, however brief, of your previous relationships. (And everyone knows that noone is completely honest when it comes to rehashing the past, and that most people will rewrite events to cast themselves in a more flattering light.) But someone like obsessed-with-her-ex-Olivia brings up her ex right off the bat. Every joke she tells, every band she enjoys, every TV show she’s binged, every opinion she espouses all relate back to this mythical Boyfriend of Yore.

Olivia knows how lovesick she sounds, and she’ll probably address this elephant in the room herself by saying something like “I know you’re not supposed to talk about your exes on a date, but I can’t help it. I mean, he was such a big part of my life for so long, and loving him has made me the person I am today!” Or, sometimes it’s not intentional, that all her favorite stories happened with her ex.

If you genuinely like who that person is despite the non-stop ex-talk – and if you don’t mind playing second fiddle to someone who’s long gone – then, by all means, ask Olivia for a second date. You might have to work a bit harder to supplant the One Who Got Away, but eventually she’ll forget him, right?

Patsy the Peer-Pressured

It won’t take long for you to pick up on the fact that Patsy’s friends are more invested in her love life than she is. They probably pushed her to build a dating profile, nagged her about checking for matches, and practically shoved her out the door for your first date. One of her besties must have written the messages you’ve been reading, too, because the woman sitting across from you bears little to no resemblance to the chatty, conversational girl you’ve been corresponding with.

Patsy clearly feels uncomfortable — it’s more than first-meeting jitters, and it doesn’t seem personal (so there’s that, at least). She just doesn’t want to be here. Maybe she’s a closeted lesbian, asexual, or grappling with her gender identity. Or perhaps she’s just shy. Some people are simply homebodies, which can make them difficult to date. If you’re an introvert as well, the two of you might make a good match. You can compare Netflix queues and banter about which is better, GrubHub or Seamless.

Hardened Hannah

Have you ever met someone who’s been burned, and badly, by a former lover — or simply by life itself — and has become cynical and jaded as a result? That’s Hardened Hannah. She wears a lot of black eyeliner and blood-red lipstick, her makeup serving as a mask. Some Hannahs favor combat boots, while others prefer wicked stilettos. She drinks her bourbon neat, and she can hold her liquor. Hannah’s eyes are dark and deep, and you can tell that they’ve Seen. Some. Sh*t. Hannah is like if Dorothy Parker, Rosa from Brooklyn 99, and a weary, worn-down, 1930s-era Appalachian mother-of-nine had a love child.

Everyone has difficulty opening up again after heartbreak, but Hannah has locked her emotions and thrown away the key. She might go toe-to-toe with you in a chicken-wing-eating contest, or drink you under the table, but don’t expect her to say “I love you” first — or ever. Nevertheless, Hannah can be a helluva lot of fun, so if you’re not looking to settle down, there’s no harm in being her FWB.

Basic Becky

Basic Beckys don’t really need much in the way of explanation. They’re everywhere these days, but especially at Starbucks, in pumpkin patches, and on Instagram. Meet your Becky at a bar, and chances are you can spot eleven lookalikes before you even find a stool.

A Becky’s music taste ranges from Billboard spot #1 to Billboard spot #10. She likes to practice self-care with a Lush bath bomb and an episode of My Favorite Murder. Becky is all about filters, hashtags, and mentions; acai bowls, avocados, and White Claws. She has a squad, and that squad has goals. When she grows up, Beckys want to be Chrissy Teigen. A couple of years back, Becky was unable to even, but nowadays that’s so 2015, and now Becky is woke (and sometimes shook).

Ain’t nothing wrong with dating a Becky, but you might have to change your name to Chad.

Final Musings

Naturally, these are all stereotypes, and there are many women who aren’t afraid to be themselves and defy convention. And you know what they say about books and their covers – so don’t judge a potential partner by the brand of shoes she wears, her makeup or hair, or the last TV show she binged. When you’re out on a date, cut her some slack; after all, she’s nervous too!

Have you ever gone on a date with one of these “types”? If so, how did it go? Any entertaining dating horror stories to share? Share your experience in the comment section!


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