5 Most Awkward Dating Situations and How to Deal

You might be hesitant to jump back into the dating scene because you’ve heard stories from your girlfriends about some truly cringe-worthy moments. But here’s the good news: with a little preparation from your trusted dating coach, you can walk into any date feeling confident, ready to have fun, and equipped to handle whatever comes your way.

I'm going to lay out the 5 most awkward situations I've helped women daters navigate in the hopes that when you encounter them, you'll be ready! And even better, because you know what to do, it will make you more excited to date in general!

This is all part of my Art of Love curriculum, designed to help women over 50 find healthy, lasting love.

1. At the end of the date, he asks you to pay or split the bill?

This can catch you off guard. Splitting the bill vs asking you to pay are two different things. If he asks you to pay on a first date, with no prior discussion, that's just weird, truly! Red flag city. If he asks you to split it, that's different; it may just be his custom, and he may be very pro-equality.

Good advice: Decide in advance how you feel about splitting and keep a little cash on hand. Prepare what you'll say if he asks. If you're cool with it, just proceed. If it makes you feel funny, because you're more of an old-fashioned girl...

✅What to say: “I appreciate the notion of equality, but I enjoy it when the person who asks does the treating.”

Then, if you like the guy, you can offer to treat him next time. And be sure in future conversations to talk about perspectives on money and equality in general, when it's not in the heat of the bill-paying moment.

➡️Pro tip: If splitting expenses bothers you, it’s better to address it early rather than letting resentment grow. Once you hide something you are upset or confused about in the relationship, you lose the ability to feel whether or not it's a good match.

2. What if he just won’t stop talking?

Some men get nervous and fill the air with lots of chatter, sometimes with lots of bragging too.  I promise the men who do this think they are entertaining and impressing you. They simply have not learned good conversational skills. You can help them!

You can steer the date back to balance by asking the right questions and sharing your own life story. Good conversations are a give and take, and where they don't need to be perfectly balanced, it's a big red flag if, with your guidance, the man you are on a date with can't listen well to what you have to say.

✅What to say: “That’s really interesting—can I tell you about something similar from my own life?” This shifts the focus naturally and builds mutual respect.

➡️Pro tip: Keep your Sparks Questions in mind so you can lead the conversation to topics that you're interested in. Practice your own answers too, so they're easy to insert when there is a pause after his answers.

3. What if he reveals a health or financial issue that’s a deal breaker?

As we age, inevitably, we will have challenges, both financial and health. In loving couples, this is just part of life's journey, and problems in these areas are solved as a team. It doesn't quite feel that way in early dating, though, and certain financial and health issues can be real stumbling blocks!

First of all, if they come up in early dating, good! That's when you want all the "liability" cards on the table! Better to confront it now rather than when you're deeply in love or your lives are intertwined. If he's revealing his secret, it's a good sign he likes you, trusts you, and you've made it safe for him to tell you vulnerable things.

But just because this will build intimacy doesn't mean it's going to be easy if the issue happens to be a dealbreaker for you. In that case, it's quite awkward because you have to kindly let them know it isn't going to work for you.

✅What to say: “Thank you for sharing that. Unfortunately, because of my history, I don't think that's going to work for me, but I appreciate your openness, and I wish you the best of everything.”

➡️Pro tip: Figure out your 3Hs criteria before the date so you know what you are and are not okay with. You can't control someone's future finances or health, but you can go in "eyes wide open" and only sign up for what you feel you can handle.

4. What if he asks about your money or health before you’re ready to share?

On the other hand, you might be the one with a financial or health issue you're not ready to discuss, and then it's very awkward if he asks you point-blank. Your personal information is yours alone until you feel safe and comfortable enough to share it.  I'd say the exception is transmissible diseases, in which case I think you have a moral obligation to disclose before you expose.

It's a huge red flag if a man is pushing to know your financial situation. There may be a good reason, like that he has had to take too much financial care of a partner in the past, but it's not a good sign if he's too pushy about it for no other reason than his own gain.

✅What to say: “I prefer to keep certain things for later once we know each other better. I hope you understand.”

➡️Pro tip: You can always redirect the conversation with curiosity about why they are asking. Probe their history to understand why it's an area of concern. You may learn so much about the context that you end up feeling comfortable showing your hand.

5. What if he hints at sex or going back to your place before you’re ready?

If a potential mate brings up sex on a first meeting or even a second date, it’s your cue to set clear boundaries. Part of the dating process that I teach entails waiting for at least 3 dates before even considering sex, and then only if you've both either agreed to be casual or agreed to be monogamous. No blurry lines!

✅What to say: “I’m not ready for that yet, but I’d like to see you again if you’re okay taking it slower.”

➡️Pro tip: The right person will respect your boundaries, and you will see their true colors as soon as you speak your truth with grace. Never get sexy before you're ready just to please a man! It has the opposite of the desired result every time!

Like anything worthwhile, it takes practice to get good at dating. I hope that shoring up your strategy for these uncomfortable situations makes you feel more ready to tackle the hard work of finding your romantic partner. I always want to build your confidence to believe in love again!

🎥 Want to date with even more confidence? 

Watch my Free Webinar: 3 Secrets to Finding Love After 50 and learn exactly how to meet the right person without wasting time on the wrong ones. 

Watch here → lauriegerber.com/webinar

FAQs

How do I avoid awkward silences on a first date?

Come prepared with your questions and your answers. Do some breathing exercises to calm your nerves so you go in calm and confident. When stress is low, good conversation naturally arises.

Is it a bad idea to meet someone from a dating app in a private place?

Yes, for the first meeting, choose a public place like a coffee shop or restaurant. It’s safer and helps you feel more comfortable.

How soon should I talk about past relationships?

It can be awkward to talk about past relationships, especially if the story isn't so pretty or doesn't make YOU look great. Keep first dates focused on getting to know each other. Sharing your full life story or details about previous partners can wait until you’ve established trust.

What are some good signs that he’s a potential match?

Consistent communication, respect for your boundaries, a sense of humor, and genuine interest in your life are all great signs. Awkward moments don't mess things up if you've found your right match!

How do I know if I’m ready for a second chance at love?

If you feel curious, open to new experiences, and willing to meet potential matches with an open mind, you’re in a better place to start dating again. And now you know what to do when awkward moments arise!