9 Marketing Lessons From the Worst Date You've Ever Been On

We've all had one.

The date who talked about themselves for 45 minutes straight, name-dropped their car twice, said "I'm not like other guys" without a shred of irony, and then texted "we should do this again!" before vanishing off the face of the earth.

Awkward, inconsiderate, and unforgettable for all the wrong reasons.

Now swap that person for your agency's marketing, and it might sound eerily familiar.

Almost every bad date move has a perfect marketing equivalent; and most agencies are guilty of at least three of them.

So here are 9 dating disasters, and the marketing lessons hiding inside each one.

1. Talking about yourself the whole time

"We've been established since 1987. We're passionate about property. Here are my 5 favourite takeaways ranked."

Cool. Nobody cares.

On a date, the person who only talks about themselves doesn't get a second one. In marketing, the agency that only talks about itself doesn't get the instruction. Your audience isn't thinking about you... they're thinking about their leaky roof, their nightmare tenant, their dream move. Make your content about their world, not yours.

Next time you film a video or write a post, try this: count how many times you say "we" and "I" versus "you." If "we" wins, start again.

2. Not listening

You tell your date you're vegetarian. They recommend the steak.

Agencies do this constantly. You market the same message to a nervous first-time seller, a buy-to-let landlord with fifteen properties, and a young couple looking to rent their first flat... and then wonder why none of them feel like you "get" them.

Good marketing starts with listening. What are people actually asking you at valuations? What questions land in your inbox every week? What keeps your clients up at night? Use those answers as your content. 

3. Trying too hard to impress

Turning up to a casual coffee in a three-piece suit. Casually mentioning your marathon time. Laughing a bit too loudly at your own joke.

The marketing version: over-produced drone footage set to cinematic music, stock images of people shaking hands in glass offices, and scripts so polished they could slide off the screen.

Here's the irony: trying too hard makes you less impressive. A genuine, slightly rough-around-the-edges video of you talking to camera in your kitchen will build more trust than a corporate reel that cost four grand. People buy genuine people - flaws, personality, and all.

4. Lying about your height on your profile

It works brilliantly. Right up until they meet you in person and realise you are not, in fact, six foot one.

Overpromising in marketing is the same trap. "We'll sell your home in two weeks." "We guarantee top price." "We'll find you a tenant by Friday." It sounds disingenuous, and corrodes trust instead of building it.

Be the agent who under-promises and over-delivers. It's not as sexy on paper, but it's the reason people come back and refer their friends. Nobody ever left a five-star review that said "they promised me the moon and sort of half-delivered."

5. Ghosting after the first meeting

The date went well. Great conversation, real chemistry, said all the right things. And then… nothing. No text or follow-up, just silence and a vague sense of betrayal.

Most agencies are fantastic at the valuation appointment and then absolutely hopeless at everything that comes after. No follow-up email, no helpful content, no nurture.

The gap between the first meeting and the instruction is where deals are won and lost. A short follow-up video, a useful piece of content, even a well-timed "just checking in" - these aren't desperate. They're what good marketing looks like after the first impression.

6. Checking your phone the whole time

There's nothing quite like pouring your heart out about your career ambitions while your date scrolls through Instagram under the table.

The agency version? Posting content but never replying to comments, running a social media account like a megaphone instead of a conversation, sending automated email replies that make the reader feel like a ticket number.

Marketing isn't a broadcast, it's a dialogue. Reply to the comments, answer the DMs, acknowledge the people who engage with you. Being "present" in your marketing means actually being there - not just scheduling posts and walking away.

7. Moving way too fast

Suggesting you move in together before the starters have arrived.

In marketing, this is the agency that jumps straight to "BOOK A FREE VALUATION" in every single post. No context, no value, no foreplay.

The best marketing is a slow build. Give someone something useful first, show them you know what you're talking about second, then - and only then - make the ask.

People don't want to be sold to; they want to feel like the decision was theirs.

8. Wearing too much cologne

One spray: attractive. Two sprays: confident. Seven sprays: people are crossing the street.

Some agencies treat their brand the way that person treats a bottle of Sauvage.

Logo on the photos, logo on the videos, logo on the floorplans, watermark across every image, brand colours cranked up to a level that could guide aircraft.

When your branding is louder than your message, people don't lean in - they back away. Confidence in your brand means you don't need to plaster it across everything. Let the content do the talking; if it's good enough, they'll find out who made it.

9. Talking about your ex the whole time

"My ex was crazy." "My ex never appreciated me." "I'm nothing like my ex."

Translated into estate agency: "Unlike other agents, we actually care." "We're not like the big corporates." "Other agents might cut corners, but we don't."

It's never a good look. On a date, it tells the other person you're not over it. In your marketing, it tells your audience you're more focused on the competition than on them.

Confident agents don't need to compare. They just show up, do brilliant work, and let the results speak. That's attractive. Slagging off the competition? That's giving them free rent in your head.

Get the Second Date

Good marketing, like a good date, comes down to a few surprisingly simple things.

Listen more than you talk. Be yourself. Don't rush it. Follow up. And for the love of all that is holy, stop mentioning your ex.

The agents who "get the second date" - the ones who win the instruction, earn the referral, build the reputation - aren't the loudest or the flashiest. They're the ones who make it about the other person.

So next time you're about to post something, film something, or send something, ask yourself one question: would this get me a second date?

If not, maybe don't hit publish.

See you next time, when I promise to steer clear of dating advice.

Toby