The Dating Coach

What I’ve Learned from 50 First Dates

Some lessons are obvious, but you'd be surprised

By Allie Roodman  February 15, 2024

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In the last two years I’ve probably gone on 50 or so first dates. I’m not exaggerating. During that time, I’ve evolved. My intentions for dating have ebbed and flowed and, in the process, I’ve learned a lot.

I’ve tried to think long and hard about what makes one date good and another terrible, or why I went out with one guy three times and another guy only once. Chemistry is awesome, but beyond those intangibles, I’ve concluded that what’s made me personally interested in a second, third, or fourth date ultimately comes down to my date’s behavior.

Unlike Drew Barrymore’s character in the movie 50 First Dates, I can actually remember mine. While I’m a heterosexual woman dating heterosexual men, the learnings probably extend beyond my dating demographic. I’m guessing you can learn from both my failures and successes.

Finally, and this is an important disclaimer, I am far from perfect, and I’m pretty sure I’ve made most of these mistakes myself.

Being Too Insecure

One of my first dates was with a man who said he was the CEO of his own business on his profile. All night long he kept using the phrase, “as the CEO.” By the third time he used it, I decided to mentally check out. I’m not a therapist, but aside from it being annoying, it felt really insecure.

On another first date, a guy asked me what I was looking for. I said I didn’t really feel comfortable sharing those details so early. He asked if maybe I was being too picky. This guy was clearly trying to take me down a notch. No thank you.

Being Rude

One time I went out with a guy, and the date was going pretty well so I was open to grabbing dinner at a second location. Things then took a turn for the worse. At the restaurant, he started to get cocky. He laid down on his side of the booth, crossed his legs, folded his arms, and proceeded to tell me how much smarter he is than basically everyone. He then paid me the compliment of “you seem pretty smart, too” — as if he was christening me into his exclusive tier of people. When we parted ways for the evening he went in for a kiss, fully expecting it to be a slam dunk, and I pulled away, hard. Delusional.

Interrupting

On another first date, one guy continuously interrupted mid-sentence  just to tell me I was pretty, or cute, or whatever. I hated this, and not because I don’t love compliments. What he was doing was trying to disarm me with flattery or something. Once, maybe. By the third time it was just annoying, and felt manipulative.

You know what’s really hot? Listening and responding. This is literally small talk 101. It’s not that hard.

Being Overly Sexual

This doesn’t need explaining.

Being Inauthentic

On another first date, it became pretty obvious to me that my date was just telling me everything he thought I wanted to hear. We met on one of the dating apps, and the whole evening felt like he was spoonfeeding me, very unnaturally, things he gathered from my dating profile. For instance, I make it pretty clear on my profile that family is important to me, and during the evening he very unnaturally figured out ways to bring that into the conversation. You get the gist. There’s a line between trying to connect, and being sleazy or manipulative. It’s fuzzy, but you can feel when it’s starting to cross over.

When he expressed some resentment over me declining a second date, I may or may not have called him a f*boy.

Being Too Chill

Anytime a guy has been a little too chill, I’m immediately less interested. I don’t know if it’s a maturity thing or a fear of putting yourself out there, but not my problem. Overall, the attitude doesn’t make me excited to go out with you again. I think a lot of women probably feel the same way.

Being Too Weird

One time I went on a date with a guy who worked in Bitcoin. In Bitcoin? I don’t know if I’m even talking about it properly here. Whatever. He also mentioned being a Libertarian. Without thinking, I made an off-hand remark that he was like a cowboy. Unfortunately for me, for the remainder of the evening, he wouldn’t let the cowboy thing go. I don’t want to get into the rest of it.

Manners

Anything that shows you’re being considerate of the other person’s feelings is a green flag. Thoughtfulness is a turn-on. I feel like I’ve dated a lot of great guys.

One time, and I’ll never forget this, I was seeing this guy who said something I found a bit off-kilter. Great guy, everything was fine, we were hanging out. And he said, “I’m not mansplaining, but I think women have too much power these days.” My brain broke a little, but I decided not to challenge him. Instead, I just sat there quietly and understood this probably isn’t my guy, and moved along my merry way.

Part of maturing is knowing when to engage, and when to be quiet.

Effort

Pretty self-explanatory. Anything that’s proactive. Anything that shows forethought, planning, and basic executive functioning skills. Attention to detail.

It’s really hot, it works. Just do it.

Confidence

Just be who you are and fully be yourself, even if you’re not interested. This might seem like a strange example, but one time this really hot guy rejected me, but in the most secure, matter of fact, respectful way. My feelings weren’t hurt at all.

My ego, on the other hand, did wrestle with it for a few weeks after, but as time passed, I started to understand his point of view more, and finally came around to think that he did us both a favor, and I actually really appreciated it.

Self-Control

Emotional control. Impulse control. Communication control. All around being in control of yourself.

One time I dated a guy who was very disciplined, structured, and respected himself a lot, in the healthiest way. Everything he did was very intentional, from the way he sat down at the table, put his phone to the side, and took off his jacket. I could not understand how someone could have so much presence of mind. Self-control is really attractive. I can’t explain it.

Dating can be fun, and if you engage intentionally and reflect on your encounters, it can teach you what’s out there, help you refine your standards, and even show you areas within yourself you might want to develop.

I’m grateful for most of the guys I’ve gone out with, as our city is full of wonderful people. Cheers to the next 50!

About the Dating Coach Column

Allie Roodman is a 31-year-old millennial trying to navigate the modern dating landscape, one bad date at a time. She uses her own experiences to help others find love in her day job as a matchmaker. She is figuring it out as she goes, just like the rest of us. Connect with her on Instagram: @allieroo

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