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7 Questions You Need to Ask Before a Second Date

7 Questions You Need to Ask Before a Second Date hernan

My mother dubbed me the “Queen of First Dates.” She always professed to be shocked if I ever “let” a guy get a second date with me. Back in my dating days, online dating was just beginning. There was a New York phone number that was called the “Rejection Line,” and I had it memorized. If someone asked for my number and I could not figure out a polite way to avoid giving it, I would dole out that number. True story: one time I gave my phone number with one number off and the guy figured it out and told me he got my number wrong. I was so shocked that he figured it out, I agreed to a second date only if my best friend could come with… you know, just in case he was a stalker. It fizzled out after that because he was too friendly and made me way uncomfortable. Needless to say, when I finally met my husband and allowed my parents to meet him, my mother could not wait to see who was worthy of me allowing him to be a part of my life.

According to several research studies, the statistics for a first date to move onto a second date is only 20-50%. That is a large margin and most studies were closer to the 20% mark. There were an abundance of articles aimed at “how to get a second date,” which, as a strong, independent woman, annoyed me. Get a second date? Girl, you are more than worth a second date. The real question is: Is that person worth a second date? The articles were quite humorous, ranging from what to talk about on the first date to what to eat and wear that leads to people wanting a second date. In case you were wondering, fried chicken supposedly led to the most second dates. So, maybe Chick-fil-A is a good idea for the 1st date? Ha! So, girl, if you feel like you are the Queen of First Dates, you are not alone; more often than not, a first date is the last date.

If you are sitting there on the first date thinking, “This isn’t so miserable… hmmm… maybe he might be worth another outing,” here are a few things to consider:

1. Is He Interesting?

As you are talking with one another, do you find common interests? Do you both like sports or traveling? Similar beliefs and morals? Or, are his differences from you intriguing? Did the conversation flow? When there were quiet moments, was it awkward?

2. Did He Ask Questions About You?

Is he interested in finding out who you are? Or, did you feel like you were on the witness stand being interrogated by the most ruthless attorney? Or maybe all he did was brag and talk about himself? I once had a guy brag about having a multi-million-dollar business and when it was time to pay for our $20 tab, his card got declined. He quickly made up some story, but I have to admit it felt good to have pulled out cash, paid for the drinks, and escaped gracefully.

3. Is He Mostly Positive?

Nothing is a greater turn off on a first date than when all you hear about is what is wrong with the other people he has dated, or problems at work, or why he doesn’t get along with a family member. Girl, that is a sign to run because most likely there is a serious underlying mental health issue. However, you don’t want someone who acts like life is perfect and as if he’s never had a problem. Let’s be real: life hands out trials and you need someone who is going to be able to have the grit to go through those journeys with you, not run away because he cannot handle adversity.

4. How Does He Speak About the Women Who Are Around Him?

Whether it be his boss, co-workers, his sister, or his mother—how does he represent them to you? I will always remember my husband describing his sisters on our first date. He spoke of them being intelligent, beautiful, kind…all-around amazing. That so impressed me. And I have to say, he was right. They are pretty phenomenal women.

5. Did You Guys Talk About the Tough Stuff?

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You know, religion and politics. Honestly, the survey is out as to whether these are topics to be discussed on the first date. I had always learned it was a big no-no. However, in today’s world, it appears to be more fair game. If you guys do end up on these topics, it is important to focus on how he discusses them. Is he judgmental and condescending as he shares his views or is he open and a good listener? I will never forget one first date when a guy brought up politics only to learn we were on the opposite sides of the fence and he belittled my views. As I am sure you already guessed, no way did he get a second date, and honestly, the first date ended minutes after the third insult. With that said, I do not believe you need to have exactly the same views to offer someone a second date. My husband and I have pretty different political views, but I love that he challenges me to think globally about my beliefs. Sometimes, it helps me solidify why I believe what I believe.

6. Is He Cute?

Yes, this is important. Did he look like he did online or was that a big lie? I am so surprised by how fake people are on their profiles. What happens when you meet up for the first time? Do they really think you are going to go out with them again when you learn that he is a big liar? On that first date, did you find him attractive? Expecting him to look like Sterling Brown, Josh Hutcherson, or Diego Boneta is not fair, but is he cute to you? Did your heart flutter a bit as you talked? Were you dreaming of kissing him and wondering what it would be like? Did you appreciate his laugh or his mannerisms? Was he a gentleman and polite to you? It does not need to be love at first sight, but you need to feel some interest in his looks.

7. Did He Respect You?

This is probably the biggest and most important, hence me saving it for last because I want you to remember this one the most. Like I said about Mr. Politics above, if he is rude to you on the first date, he is definitely not worth a second date. Did he have manners? Did he appropriately compliment you? Did he respect your boundaries and read your body language? If you don’t like to kiss on the first date and he did not push for a kiss, then good. Did he demand to take you home and show no respect for your desires when you wanted to take an Uber and you made several attempts to politely say no? Or, did he notice you scheduling an Uber and offer to take you home, which you felt safe doing and found to be polite? Trust your gut on this one, ladies!

Overall, it is important to strike a happy balance. Shooting every guy down because he didn’t check off every box of your 101 items of what you expect in a guy may keep you from meeting the right person. If he met at least 50 items, give the guy a second chance. You may find that he had even more items, but you were too focused on the ones he didn’t meet. However, if your gut instinct after the first date is that took a lot of grit to get through, then your answer is probably no. Also, keep in mind, it is important to show grace in letting someone down. You can be polite, while firmly saying no thank you.

Want more insight into dating? Check out:

Here’s a Quick Way to Know If You Should Keep Dating Him
He Brings Me Flowers, but Is That Enough?
5 Guys to Avoid (That Your Mother Warned You About)

 I Said I Would Never Date Again, but Then…
7 Things to Look for in a Man
My Story, Daring to Date After Divorce

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You’ll love this podcast episode from This Grit and Grace Life: Dating? What to Look for in a Man – 073!

Feature image by Hernan Sanchez.



Dr. Christina is a licensed psychologist in a private practice who mostly specializes in children's issues as well as family law. She’s a Midwestern native, wife, and mom of two living in Florida who travels north often to enjoy the beauty of the seasons.

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