The Worst First Date Mistakes (And How To Bounce Back)

The Worst First Date Mistakes (And How To Bounce Back)

Online dating has made meeting people easier than ever, but that also means one little mistake can mean the difference between a second date and someone moving on to the next match. From forgetting your wallet to going in for the kiss at the wrong time, a first date is a minefield. Here are some common first date snafus, and how to recover when they happen to you.

Illustration by Sam Woolley.

You’re Late, You’re Late, for a Very Important Date

You should always leave early for the first date (or any meetup for that matter). Even so, the saying goes: “I’m the world and I don’t give a shit about your plans,” and life can get in the way. When you’re running behind despite your best efforts, not all is lost. There’s still something you can do to stay in your date’s good graces.

Vanessa Marin, licensed marriage and family therapist and Lifehacker contributor, suggests you send an apologetic text as soon as you realise you’re going to be late. Again, not when you’re already late, as soon as you realise the inevitability of being late. If you can, give them an ETA and overshoot how long they will have to wait for you. As Adrian Furnham, Ph.D., a professor of psychology at University College London and the Norwegian Business School, explains, people don’t mind waiting as much if they know how long they have to wait, and if their wait ends up being shorter than they expected. Marin also recommends you apologise again once you arrive:

Apologise once you get there as well. You can even use the situation to set up a second date, if the first one goes well. Say something like, “I really owe you one for being late today. Would you let me make it up to you by taking you on a killer second date?”

Dating columnist and Kotaku contributor Dr Nerdlove suggests you dig a little deeper if you get that second chance. Check Waze or Google Maps to see what traffic is like as it gets closer to your meeting time (Google Maps even estimates departure times and your commute using historic traffic data), and take a few minutes to familiarise yourself with the area, streets and possible parking zones so you’re not scrambling for a spot when you arrive.

If you’re running late because something really bad happened (your car broke down, you’ve been asked to work late, family emergency and so on), just cancel and reschedule. You don’t want to make them wait for more than 15 or 20 minutes max, and you certainly don’t want to meet them while you’re in a bad mood because work got a hold of you, or dirty because you had to change a tyre. Just be sure to let them know as soon as the problem pops up so they can still make plans to do something else. Courtesy goes a long way here.

You’re Not Sure If It’s a Date or Not

It’s hard to have a great first date if you don’t actually know it’s a date. This is less of a problem if you met the person through an online dating service (obviously you’re both there to find a date), but it’s a fairly common issue when meeting friends of friends or even spending alone time with someone who’s already a friend. Either way, get this figured out as quickly as possible, says Marin. If you can get some clarification before you meet, do so. If not, don’t let too much time pass before you ask once you meet up. It’s awkward to bring it up, but it will only get worse as more time passes, suggests Marin:

After you’ve said hello and settled in, say something like, “I’ve been really looking forward to spending more time with you, but I have to admit I wasn’t sure if we were hanging out as friends or if this was a date.”

Be prepared for their answer to go either way. If they say yes, great. If they say no, at least you know the pressure’s off. You’re better off talking about it like an adult.

You Run Out of Things to Say, or You’ve Been Talking Nonstop

A good first date should be like good radio, no dead air. Sure, there will be a few commercial breaks here and there, but unless you’re staring into each other’s eyes while a love song plays for the audience, you guys should be actively engaged with each other. You’re trying to get to know each other, and you can’t do that if you don’t talk.

So, when your old friend awkward silence jumps in as the third wheel, Nerdlove suggests you use some open-ended question prompts like:

  • Tell me about”¦
  • How do you”¦
  • What inspired you to”¦
  • What’s $SUBJECT like?
  • Why”¦
  • What’s the best part of”¦
  • Have you”¦ /Did you”¦

When they answer your questions, practice active listening and wait for your turn to speak. It doesn’t hurt to rephrase what they said to make sure you understand. As Nerdlove explains, you can use their answers as springboards to other topics:

You can almost always segue into another topic with “you know, that reminds me,” and sharing a little about yourself in order to invite reciprocity from them”¦ Just be sure to not go into interviewer mode by alternating questions with statements or relating to what they have had to say.

Of course, if you’re drawing a blank, Marin says that giving a polite compliment can be an easy way to break the silence. Something as simple as “I’m sorry, I just got so distracted by how pretty your eyes are, and lost my train of thought” will do. That example is a little on the cheesy side, but you get the idea. Don’t overdo it or make yourself sound creepy.

If the opposite is happening, and you can’t seem to shut up, it’s OK. Once you recognise it, Marin suggests you acknowledge it and brush it off quickly with something like “Wow, well that’s more than enough about me. I’m way more interested in learning about you.” Then you can segue into a question. In the same vein, if you start revealing a bit too much about your personal life or dating exploits than you think you really should reveal on a first date, stop yourself and say something like “That’s probably a little more information than you need at this point!” A laugh or smile will help ease the tension, then ask them something about themselves. Odds are, you actually want to learn about them, and getting them talking takes the pressure off of you to perform, so to speak.

There’s Just No Chemistry

You meet up, you have a nice chat, and…nothing. It’s OK, it’s bound to happen, especially when meeting people for the first time. Nerdlove explains that if there’s no chemistry, there’s no shame in calling it a night early:

This is one reason why going for drinks or coffee makes for a better first date than dinner – it’s less of a time investment and it’s easier to make your apologies and leave when you aren’t in the middle of an entree. Just realise that everybody and their dog knows about the “emergency call” trick. It’s less insulting to say “Hey, it’s been nice meeting you, but I’ve got to go.”

You might think you’re being nice by powering through the rest the of the date, but you’re really just wasting everyone’s time, and worse, you might make the other person think you’re actually enjoying their company when you really don’t. If you want to spare their feelings as much as possible, Marin suggests you keep things vague and say something like, “I think you’re a great person, and I want to be honest with you. It feels more like a friendship type of connection between us. Thanks for spending time with me tonight.”

Furthermore, both Marin and Nerdlove agree that you should be totally honest about further plans. Don’t say “I’ll call you” or “We should do this again sometime” just to keep things from being awkward. When we asked Lifehacker readers about their biggest first date mistakes, a lot of commenters said theirs was agreeing to a second date when things didn’t feel right on the first. Forcing things doesn’t work out for anyone.

You Pick a Bad Venue

If you do your homework with sources like Yelp, Foursquare, Google Reviews and even those free alternative weekly papers on your area, you’re less likely to pick a bad venue (pro tip: Nerdlove recommends you pay particular attention to what reviewers say about noise level). Even a decent venue can throw you a curveball, however. For example, a highly-rated bar with a “cosy, quiet atmosphere” is great for a date, but unforeseen special events like karaoke, trivia nights, reserved parties, live music and comedy nights (avoid comedy clubs at all costs) can derail your plan fast.

This happens more often than you think, says Nerdlove, so always have a contingency plan ready. That way you can smoothly transition to a different location without having the awkward “so, where now?” conversation. Personally, I have an ever-growing list of bookmarked places in Yelp that I know will be fun date spots in case our first choice doesn’t work out.

If you don’t have a backup plan ready, Marin suggests you make finding a new place an adventurous game:

Pull up a list of highly-rated nearby places on Yelp or Foursquare. If you pull up, say 10 results, ask your date to randomly pick a number from 1-10, then go to that place.

If you can’t leave the venue you’ve chosen (maybe it’s a show or you paid a cover and you don’t want to waste the money), Marin says it’s the perfect opportunity to bond over how bad the experience is. Make up stories about the other people around you, or joke about the bizarre atmosphere. A bad experience can also be a chance to secure a second date. Say something like, “I owe you a really awesome second date,” and make sure you do a little more recon for next time.

You Forget Your Purse or Wallet

You’re having a grand ol’ time with your date when the check comes, you reach for your money, and it’s gone. What do you do? For starters, Marin says you should apologise profusely, and mean it. Whether you were planning on paying for everything or not, you’ve now forced it all on them. Explain that it was an accident and try to find a way to make it up to them. If you have a banking app, for example, send your portion over to them on the spot. If they’re understanding about the whole thing, use it as an opportunity to plan a second date and offer to pay for it all next time.

If you want to avoid something like this from ever happening again, Nerdlove suggests you put together an emergency date kit that you can keep in your car. Keep a stash of cash (for times like this), as well as other helpful items like antihistamines, decongestants, mouthwash, indigestion medicine and a travel-sized deodorant. Basically, you want a dating utility belt so you’re always ready for anything.

You Start Talking About Your Ex

Try as you might to block them out, exes leave a mark, and it’s only natural for them to come up at some point. Odds are you spent a lot of time with them, so you have shareable stories that involve them. Even so, talking about your ex is a quick way to end a date. In fact, it’s one of the biggest red flags people look out for on a date.

If you catch yourself talking about your ex, the only thing you can do is acknowledge it and change the subject. Marin recommends you turn it into a compliment before changing the subject. Say something like “I’m sorry, I shouldn’t be talking about my ex on a first date. You’re such a good listener! I’m apparently comfortable talking to you about anything.” Then you can ask them a question or shift topics. This trick lets your date know that you are actually more interested in them, quite over your ex and that they’re also a good listener.

You Go for the Kiss at the Wrong Time (or Don’t When You Should Have)

The night is over, and you’re about to part ways. You decide to go in for the kiss, then they back away like there’s a spider on your face. Don’t panic, says Marin. Just keep it simple, say that you’re sorry, and let them explain if they want to. They may have a no-kissing-on-the-first-date policy, or maybe the timing just wasn’t right. Don’t take it personally and don’t make a big deal out of it. If things get awkward, Nerdlove recommends you acknowledge it and play it off like it’s no big deal:

People will usually look to you for an example of how to react to things; if you don’t make it weird, they won’t make it weird. Don’t don’t pull back or make a production out of it. The more attention you bring to the mistake, the bigger a deal it will become.

By apologising and brushing it off, it turns an awkward mistake into a blip in the night that everyone will forget about.

So when should you go for the kiss? It depends on the date and how well things are going. Nerdlove notes that reading body language is key to knowing when it’s OK to kiss someone:

The eyes and mouth are the two biggest giveaways. Someone who wants to kiss you or wants to be kissed will be calling attention to their mouths – licking their lips or biting their lip, particularly if you’re close to them. They will also be looking at your mouth. One of the surest signs of interest in kissing is what’s known as the Triangle Gaze: their eyes go from your eyes down to your mouth and back to your eyes again.

If you’re getting those kinds of signals, it’s probably a safe time to try for the kiss — especially if you’re at what feels like a high-point of the date. Be sure to move in slowly, however. Doing so will be more romantic and exciting, and as Nerdlove explains, it gives them time to wave you off or give you their cheek. If the date is winding down and you think you missed an opportunity to go for the kiss, Marin says you can play it off coolly by saying something like, “I feel like I just missed my moment there. Can I try again?”


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