Two Relationship Experts Analyzed My Texts With My Dates & Were Creepily Spot On

Genevieve Wheeler

Dating in 2018 has its pros and cons, and sitting at the top of both lists is the complete transparency of it all. We can vet our dates more easily now than ever before: Skimming a person’s resume on LinkedIn, sifting through years of spring break photos on Instagram, capturing every conversation (seriously, every conversation) with screenshots — screenshots we then tuck into our dating archives to be analyzed for weeks, maybe even years, to come. I had two relationship experts analyze my texts with my dates to see what their findings would reveal about my connection with each one.

See, I have a pretty bad habit of passing my phone around the brunch table (or study lounge, or group text), asking every one of my friends what a guy’s messages might imply about our hypothetical, budding relationship.

“I feel like, he’s just not as excited about this as he should be, you know?” I’ll ask, which usually leads to a few firm reminders that it’s just a first date (and the majority of the texting population is a bit more conservative with their use of excited ALL CAPS MESSAGES than I am).

In addition to the reminders that I should probably lay off the caps lock, these in-depth text analyses also mean that I sometimes — cough, always — walk up to dates with a set of preconceived notions about a person I’ve never even met, about a relationship I haven’t even entered. But is that habit a healthy one? Am I helping or hurting my own chances of hitting it off with these guys?

Let’s find out.

I turned to two relationship experts and asked them to analyze my text exchanges before or after my first dates with three different fellows: Tom, Will, and Rory. I’d stumbled across each fellow in the same way (on dating apps, because of course), though their dates had completely different outcomes.

Here’s what Lori Salkin, senior matchmaker and dating coach at, and Dr. Fran Walfish, family and relationship psychotherapist, author of The Self-Aware Parent, and co-star on WE tv’s Sex Box had to say on the matter. I won’t tell you how the dates ended just yet, but — spoiler alert! — these pros know their stuff.

Tom, The Recently Promoted Finance Bro

Genevieve Wheeler

First up we had Tom, an exceptionally handsome finance bro who was far from my usual type. Tom had initiated the switch from dating app convo to text by suggesting we “Grab a drink sometime” and slipping his phone number into the next message, which is where this message picks up. (After I’d waited a crisp 24 hours, that is.)

“From the get go, Genevieve, you are trying too hard to pin this guy down,” said Dr. Walfish. Yikes.

Genevieve Wheeler

“You initiate the friendly call while he is evasive and non-committal to get together," she continues. "You go overboard in kindness by congratulating him yet again (my count is three times, if you include ‘We’ll have something to celebrate’). To me, Tom comes across as self-absorbed.”

Salkin, on the other hand, noted that, “Genevieve is a woman leading this generation in women’s equality!” (You’re welcome, women everywhere!) “I would still caution her to make sure she knows Tom is not following the old-school rules of dating… So far, it seems Tom has a bit of a strong personality… as he is quite braggadocious.”

Again, I’m not going to tell you how our date turned just yet, but keep this in mind, all right?

Will, The Man of Few Words (Er, Texts)

Genevieve Wheeler

Full disclosure: I wasn’t super jazzed about my date with Will. I’d agreed to meet him one night during a crazy busy week, completely forgetting that I had a guest lecture for my grad program scheduled that same evening. (It wasn’t really rescheduled, I just totally forgot! Don’t judge me!) That said, I felt awful shifting our plans around, which I strived to express with a series of exclamatory messages and repeated apologies.

“[You] definitely seem to be lot chattier than he is over text,” noted Salkin. Not untrue.

Genevieve Wheeler

“Genevieve, you own accountability by saying you are ‘the WORST’ at the top of your note, and then you kindly ask for a tardy pass or rain check,” said Dr. Walfish. “Will responds good-naturedly and openly without any ego defensiveness. He doesn’t react as if he feels rejected. Instead, Will shows flexibility … These are my anticipatory cues that we have two essentially open, willing partners in Genevieve and Will.”

So, we appeared to be open and willing — albeit flustered. Noted.

Rory, The Upside-Down Smiley Emoji Fan

Genevieve Wheeler

Next up we’ve got Rory, who’s a big fan of that upside-down smiley emoji. (Is anyone else unclear on what this expression is trying to convey? No? Just me?)

Genevieve Wheeler

“Rory seems like [a] good guy,” Dr. Walfish commented. “He is concerned with what you like and want for a meeting place.”


Genevieve Wheeler

“Rory also clearly is eager to go out a second time, so much so that he said as much [at] the end of the first date,” said Salkin. “Most girls love it when the guy is confident and gives an indication that he wants to go out again, but others say that it comes at the risk of being too overly eager and not having any ‘game.’ It worked for Rory and [you seem] to love someone confident… as [you] also [don’t] seem to be worried about being eager.”

Not being eager has never really been my forte (remember my affinity for caps lock?). Let’s see how this equal eagerness plays out.

The Results

Drumroll, please!

Both of our experts were completely on the money when it came to pretty much all of these dates.

Tom, who Salkin called “braggadocious,” and Dr. Walfish pinned as seemingly “self-absorbed," was exactly that. He def wasn’t following the “old-school rules of dating.” He spent most of the night describing the ways in which he was “crushing” it at work, and when the check arrived, said, “You’re covering this, right? As a celebration?”

I’m not sure if this was the result of some majorly misplaced BDE (we, obviously, did not make it far enough into a pseudo-relationship for me to find out), but this guy clearly had no interest in wooing me, which our early texts pretty clearly suggested.

Will, whose few messages indicated he was an “open and willing” potential partner, was… way too cool and chill for me. He’d taken a semester off in college to go surfing in southeast Asia, played guitar in a friend’s indie rock band, and seemed like the type of guy who would have a Mandala tapestry draped behind his bed. Admittedly, I was drawn to his cool, calm, and collected disposition in the moment, but I think he was overwhelmed by my — well — very uncool, un-calm energy. This date served as yet another reminder that opposites don’t always attract, no matter what Paula Abdul might have us believe.

Finally, Rory, who Dr. Walfish dubbed a “good guy," definitely was (well, is) a good guy. He was the only one of these fellows who shot me a post-date text and made plans to go out again, and again, and again in weeks to come. As Salkin pointed out, our eager energies matched each other’s pretty nicely, which likely explains why our date was the only one that ended with a semi-happily-ever-after (or the start of one, at least).

Honestly, I kind of expected the results of this little experiment to be inconclusive. I thought Lori Salkin and Dr. Walfish would explain that there wasn’t enough to read into from these messages — that nothing could really indicate how our dates would turn out. But the truth is, there is something to be said about the way someone communicates even before you’ve met IRL. You’ll never really know how well you and your date connect until you speak in real life, of course, but you can definitely get a sense of their personality in these early exchanges.

Cue the brunch-table-phone-passing.

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