Here’s How to Get a Second Date When the First One Sucked

First Date Fizzled? Here’s How to Earn Yourself a Second One

Sometimes in a relationship, you’re not sure how to phrase a delicate subject or tricky topic. Sure, saying nothing at all is easy, but avoiding the subject doesn’t do anyone any good. Awkward Conversations provides you with a template for what to say — and what not to say — and why, so you can have those difficult discussions without them turning into full-blown fights.

Sometimes, you go on a date with someone promising, but factors out of your control have it fizzling out real fast. Maybe it’s the fact that you picked a noisy restaurant, leaving the two of you to scream at each other across the table, or you were just feeling under the weather after a particularly frustrating work day. 

Whatever the reason, you didn’t immediately click, and now your date isn’t interested in a second one. Luckily for you, here are some handy tips on how to get them to give you another chance. 

1. Consider What Went Wrong

First, you need to assess where the date went wrong. That way, you can address it in your follow-up text (if you really think it’s something that needs addressing). What made the date bad? Did your date get very quiet when you brought up politics? Was the bar you chose was too crowded? 

You might not know what the issue is or was, but taking some time to think about it might produce a clue about where things went wrong. And if you really have no idea, it doesn’t hurt to get some clarity by asking. 

2. Start With an Apology

SAY: “I know you were probably not expecting to hear from me again, but here’s the thing: I really enjoyed meeting you. In fact, I think you’re great, and I’d love to go out again.” 

Deliver an apology that’s short and sweet before moving on to something complimentary. While this will demonstrate your thoughtfulness, it doesn’t mean you have to grovel too much. No one likes the smell of desperation, and you certainly don’t want to be in the position of begging someone to go out with you. 

3. Keep It Light-Hearted

SAY: “I’m sure you were a big fan of me accidentally spilling that drink down your shirt (so sorry, again!) If we go out again, I promise not to make any sudden movements.” 

If the first date was pretty cringe-worthy, your follow-up message is going to be slightly awkward no matter what. That means there’s no harm in using this opportunity to be a little goofy. Making light of the situation is a good way to defuse the tension (and also show them that you don’t take yourself too seriously). 

4. If You Were Nervous, Say So

SAY: “I was looking forward to our date so much, but first dates always bring out the nerves. I’m much more outgoing, but that’s really why I was a little awkward meeting you on our date.” 

Nerves have wrecked plenty of dates, but that doesn’t mean you should be embarrassed of having the jitters. You don’t need to hide it. In fact, being honest about how nervous you were is actually kind of endearing.

If you tell your date about your nervousness, at least they won’t have to wonder why you were so quiet and awkward all night. Speaking up might even put you at ease.

5. Don’t Talk About Chemistry or Compatibility

SAY: “You can’t tell if you like someone based on just one date! That’s why I think we should go on another date. I know we would really hit it off.” 

Be confident, not cocky. As you can’t guarantee that sparks will fly on the second date, it’s best to just ask for a second chance without explaining why you two would be the perfect couple. 

6. Don’t Brag About How Great You Are

DON’T SAY: “Hey, I know you told me that you’re not interested, but here’s why you should change your mind: I am a very successful investment banker, and I have a much better sense of humor normally than I did on our date.”

That text? No, no, no. Don’t rattle off all the reasons you’re actually dateable. This sounds extremely cringeworthy and only serves to worsen your case. Show, don’t tell! Instead of coming up with reasons why you’re a catch, you can just explain why you might not have been at your best during the first date. 

7. Don’t Put Pressure on Your Date

SAY: “I know I picked the worst possible place for our date – would you be at all interested in a re-do? I promise the place won’t disappoint this time.”

Texting someone who’s already turned you down (especially if it’s a woman) is extremely risky. You don’t want to seem like one of those guys who can’t handle rejection — that’s the biggest possible red flag

Make it very clear from your text that you’re chill and respectful of your date’s boundaries, even if you don’t love the final outcome. 

8. Don’t Send a Wall of Text

DON’T SAY: “I’m kind of in a weird place right now. I’m still getting over my last ex — I think that might have affected my mood during our date. Also, you said something that reminded me of my boss at my last job who was always telling me I was incompetent. Being laid off a few months ago was really hard. Have you ever been laid off? Let me tell you what it’s like…”

Yikes. Don’t inundate the other person with long paragraphs explaining why your date wasn’t great, or why you deserve a second chance. You don’t know each other well enough for that yet, and if you overwhelm them now, you’ll likely never see them again. 

Instead, show that you value their time by composing a short and polite text. Get right to the point of asking them out on a second date. 

9. Suggest a Different Kind of Date

If you went to a restaurant or a bar for your first date, try something different this time around. Look up cool events or shows happening in your city and invite your date to one, or consider one of these unique date ideas.

Putting some thought into it will demonstrate your interest in them. Also, it will feel like the fresh start you both need. 

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