
Looming in front of you is another first date with another person who may be “the one”. That means another first date conversation is also looming.
Your hopes are high, your anticipation palpable. You hope she or he will be the one, so you can get off the dating merry-go-round.
You’ve planned what to wear and, if you’re smart, some things to discuss to break the ice.
You think you know what to say and do on a first date, but do you really?
You may decide it’s best to lay it all out there, telling everything bad and good about yourself, as a strategy to weed people out.
Your thinking may be that if they don’t like who you are, warts and all, they’re not right for you.
But that approach could lead to more than your share of first-and-only dates.
How to approach a first date conversation
You may have been introduced to your date by someone you know.
Or you may have met them on a dating site like eHarmony, our readers’ favorite online dating site.
Or you may have randomly met them somewhere, struck up a conversation, and decided to go on a date.
However it happened, your first date mission should be to make things as pleasant as possible for both of you.
Keep things easy-breezy, positive and upbeat.
Don’t do or say things that clearly show you’re assessing them. No one wants to be scrutinized on a first date.
Remember. It’s just one date so lighten up!
You can get enough of a feel for someone to know if you want a second date just by having a casual conversation with them.
Cosmo wrote an article with a whopping 97 things NOT to say on a first date, but let’s look at some specifics:
10 of My Pet Peeve First Date Conversation Killers
In my years of dating experience, I was often amazed by what men came out with on our first date.
1. Swearing like a sailor.
Don’t get me wrong. I like to swear. It’s powerful and serves a purpose, when used with care.
Some swear words, especially the harshest ones, fit the bill perfectly for venting or to add emphasis to something I’m saying.
But I would NEVER swear in front of someone I’ve just met . . . or even someone I’ve only known for a short time.
Certainly, I would not swear on the first date, or the first several dates.
And there are some people I would never, ever swear in front of.
On one first date of mine, the man launched into a mini-tirade about something, and let loose with some hard-hitting expletives. Unfortunate, because things had been well until then.
I was turned off and on high alert for other red flags . . . which followed in rapid succession after this first offense.
He easily slid into my #2 pet peeve conversation killer. Read on.
2. Talking about sexual preferences or sex at all.
If either of you are talking about sex on the first date, chances are you’re contemplating having sex on the first date.
I can’t think of a time or situation when that’s a good idea.
If you’re looking for true, abiding love, the first few dates with anyone should be about getting to know them and determine whether or not they’re someone you can live and grow with.
If your goal for dating is hopping through a serious of one-nighters, that’s a different story, and perfectly fine to do, as long as you’re upfront about it from the beginning.
Otherwise, sex and sex talk too early may sabotage any chance for a relationship to blossom.
My date noted in #1 above began talking about another first date he had. One woman in particular over-imbibed and made overtures to him.
Using profane language once again, my date related in explicit detail the woman’s advances on him. To me, sitting there listening to him, he came off as sleazy and opportunistic, because he enjoyed watching this woman embarrass herself.
3. Saying something judgmental or insulting to your date.
Towards the end of my first date with the same man I noted above, he talked about taking me to a favorite jazz club of his.
“But”, he said, “you’ll have to wear make-up and nicer clothes than this.”
Not that it matters, but I was wearing make-up, as much make-up as I ever would. And I was wearing something that would be perfectly fine to wear to a club.
You’ve probably heard an apt saying for this situation:
“If you have nothing nice to say about someone, say nothing.”
But especially on a first date when both of you should be putting your best foot forward.
If this guy could so easily put me down on date one, imagine what future dates would be like.
In the end, I was thankful that he showed his true colors so early in the game.
4. Telling crude or suggestive jokes.
You may think this is a good idea because you want to judge whether they appreciate your sense of humor.
On a first date you just don’t know what someone will find funny or be offended by. So why risk it?
Why risk turning them off before you give them the chance to know the whole you?
Getting a feel for each other’s personalities develops over time.
5. Asking your date inappropriate questions or things it’s way too early to talk about.
First dates should be casual, let’s-learn-about-each-other meetings. Even light conversation can help you assess that person.
As you’ll see later in this article, you don’t need to know about things like:
- Past failed or unhappy relationships
- Money and finances
- Family problems and issues
- Where and how they live
- If they’re dating other people
Save the big things like this for later in the relationship, if it advances beyond the first date.
6. Discussing your medical issues.
Your date (probably) doesn’t want to hear about your various medical woes.
Doing this marks you as self-centered and self-absorbed.
I’ve sat across from enough people who dwell on their ailments to know that it leaves little room for balanced conversation.
Negative talk like this should be avoided.
7. Telling your date they look just like your late spouse.
It makes me cringe just thinking about this one.
Someone who compares you to their dead wife or husband may not be ready to date. They may still be grieving. So tread lightly here.
8. Neglecting to smile often and make eye contact throughout.
As I mentioned above, your mission should be to make this as pleasant an experience for both of you as possible. Even if you know from the start this person is not right for you, and there’ll be no second date.
The more you enjoy yourselves, the more you’ll be smiling, which is always an attractive, inviting feature to see on someone’s face.
Isn’t it better to leave a first-and-only date feeling good about it?
Maybe you’ll learn a little something about yourself and dating, instead of walking away feeling bad and thinking you’ve had one more failed date.
9. Reading from a written list of questions.
I remember one first date that was going along well enough. Although I knew pretty quickly I didn’t want a second date, we were having an enjoyable conversation, so I consider that a successful first date.
Then he pulled out a typed list of about 20 questions to ask me and started going down the list.
Suddenly everything felt formal, like I was at a job interview. He disrupted the nice flow we had going.
Even though I said something sarcastic like “This feels like a job interview”, he plowed ahead and clearly thought he was acing this interview.
So much so that, when we were saying goodbye in the parking lot, he grabbed me and kissed me on the lips. I gave him no indication that I wanted this. Clearly, he misread my kindness towards him for attraction.
I think it’s a good idea to put together a list of questions beforehand, but put them aside for the date. Take a quick look at them before you go into the date to refresh your memory.
10. Talking politics in an aggressive way.

Especially in today’s polarizing climate, talking politics on a first date is risky business.
Unless you’re both perfectly aligned politically, this kind of talk will probably be controversial and debatable. Things can go downhill in a heartbeat and become argumentative.
Remember being told never to discuss politics at the family Thanksgiving table? The same rule applies in dating.
Think about it. If you have no indication of your date’s political leaning, but bring it up anyway and want to discuss your viewpoint at length, a few things can happen:
- Your date entirely agrees with your point of view and likes you even more because you’re on the same team.
- Your date entirely agrees with your point of view, but is turned off by your heated approach.
- Your date agrees with some of your talking points, but is turned off by your heated approach.
- Your date is diametrically opposed to your beliefs and is overcome with the desire to run.
The odds will be stacked against you. Why take the chance?
I feel couples can be politically opposed and still have a loving, healthy relationship. But that will only happen if both people respect their different political leanings, and avoid political rancor and arguments entirely.
Someone who needs to bring up politics so early in the game, to determine whether to rule out their date, is probably not the kind of person who could handle a partner who had different political leanings than them.
More ways to blow your first date conversation
Avoid heavy topics, such as these outlined in an article by blogger Lindsay Tigar (the page is no longer live). She suggests waiting until much later in the game to broach such topics:
Talk about your exes.
“Discussing the past so early into a could-be relationship is like throwing water on a flame that’s barely starting to fluster.”
In depth musings about your future together.
“Before you put the cart way ahead of the horse, take a breather and savor the moment of the first date. If he does happen to be the guy you’ll spend forever-and-ever with, this is your last first date… ever. So enjoy it!”
Queries about money and personal finances.
“Nothing takes the fun, energy or romance out of a good date like dropping the ‘how much do you make in a year?’ or ‘do you eventually want to buy a home of your own?’ question prematurely.”
Belaboring family problems and issues.
“Bringing up heavy family topics (like sickness or feuds) is too personal for the first date. While it might not seem like a big deal to you, family matters are intimate details that shouldn’t be shared with just anyone.”
Leave a Reply