Should You Go on a Second Date?

Wondering if you should go on a second date? It’s like trying to decide if you should eat that last slice of pizza – you’re not sure if it’s a good idea, but you’re also not ready to let it go.

Sometimes it’s just not clear. Deciding whether to go on a second date can be a tough decision. After meeting for lunch, you may have found the interaction enjoyable but lacking that special spark. Perhaps during a drinks date, you were attracted to your date but felt like they dominated the conversation without asking about you. Or maybe during a coffee and walk, there were awkward pauses that made you question the connection.

Despite these factors, your date reaches out the next day expressing interest in seeing you again. How do you assess the first date and determine if a second date is worth your time? Let’s explore some key questions to consider, but first, let’s address some factors that may have influenced your perception of the date.

Going into the Date with Sky-High Expectations

Over the past two weeks, I had this occur twice with clients in my dating coaching program. One 66-year-old client talked on the phone for 90-minutes* prior to the date and was “in love” by the end of the call and could not wait for the next day’s dinner at a fancy Chicago restaurant her date had booked. Not only that, she called and told 5 friends (and me) that she’d met The One! (I bet this man sensed the wedding bells clanging as she walked into the restaurant.)

So, what happened? He turned out to be attractive – until he talked about himself for two hours, never asked about her except to ask if she’d go topless at a French beach. What?

My point: Go into every date with no expectations.

I know what you’re thinking: What? That sounds negative, Andrea. Nope, it’s not. It’s the best thing you can do – high expectations are rarely met – and low expectations are the negative clincher. Zero expectations beyond looking forward to meeting a new person – that’s the ticket!

*My tried-and-true rule as my clients know: 10 minutes max. The phone call is nothing more than a “let’s chat for a few minutes and see if we’d like to meet in real life.” I’m a fan of no phone calls when possible – unless significant distance is involved.

I’m-Beat-Up-From-Online-Dating

You’ve been on Bumble, Hinge or Our Time for 3 months and your membership ends next week. You haven’t met The One. You show up on dates and just can’t help yourself from bashing online dating.

Let me tell you something: No one loves online dating until they meet someone. Then it’s the best thing they’ve ever done.

Ever hear the line often used with entrepreneurs in business: “Fake it ‘til you make it”? I’m a fan and have done this many times at the beginning of my career as I nearly went bankrupt several times in the early years. But when I was at a party and someone asked me, “How’s that dating lunch thing you started going?” My answer was always, “Fantastic – I just went to a wedding last week for two of my clients.” (True, but I was hanging on financially by a thread.)

No date wants to hear your sad online dating stories. Actually, nobody wants to hear them – except maybe your girlfriend who has been single for 20 years and relishes doom and gloom stories.

7 Questions to Ask Yourself Before You Go on a Second Date

Did You Feel Chemistry?

Ok, that’s a trick question for you. Maybe you remember a recent article where I talked all about chemistry. Based on nearly 30 years of dating expertise, many find chemistry on the 2nd or 3rd date.

Are You on the Fence?

Maybe you are 50-50 on whether to give it one more shot. If I work with you, you know all about my 1-100 scale. On the fence – yes, you go on a second date as the pendulum will swing one way or another after this date.

Did You See Any Red Flags?

Ok, this one can be a definite deal-breaker. A 63-year-old male client went on a lovely lunch date with a woman who was separated, very attractive and a good conversationalist. They had much in common. But then she disclosed that her divorce proceedings were acrimonious and looked to go on for a year or two. My client (smartly) decided to move on and not get involved in this mess).

What Is Your Intuition Saying?

You are smart and not 22-years-old – you have life experience. Don’t discount intuition.

And maybe it’s time to pull the trigger and finally do a 15-minute call with me.

Are Your Lifestyles Compatible?

Realistically, you very well may not know this from a first date. Here’s an example of one that maybe should not have worked out (but it did):

My client Michael is 69, Jewish (non-practicing except occasionally), divorced with 3 grown children in their 20s. His date, Laura, was never married, no children, and Catholic from a large family. But her profile said she loves children and still spoils her nieces and nephews who are grown adults.

As Michael told me, “Hey, I’m not having kids with her, she likes my children and has embraced my family at gatherings.” They got married in March 2023. Yes, Michael was initially reluctant to go on even a first date as she wasn’t Jewish, had no kids and never married. Then, while attracted to Laura, he was on the fence as to the second date as well. A gentle push came from me.

He’s still in touch and just sent me photos of the whole family, vacationing in the Maldives, looking very happy two weeks ago!

What’s the Downside of a Second Date?

If you are asking this question, there probably is not one. Give it a second chance. It’s not a marriage proposal, it’s a second date. Too many people think fireworks should go off on a first date – when actually, as you hit 2nd Acts in dating a slow burn works just as well.

Did You Go on the Date with a Checklist?

If you did, burn it. Instead, evaluate:

Was the conversation fun?

Did I laugh?

Was I curious to learn more?

Was I engaged?

Think about how you felt on the date, not did they check off 5-10 must-haves on a list.

In general, what’s my answer? If you are asking this question – Should I go on a second date? – GO!

Questions for the Community:

Do you have a must-have list that you go by on dates? Is it longer than 4-5 items? When has chemistry happened for you?

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