Dating Tips for the Second Date - Cool Dating Advice

Dating Tips for the Second Date

So you made it through your first date and you are ready to go on your second date. The second date should be a time to connect even more and maybe get a little more personal. If you are interested in a second date, make sure you follow up after the first date unless of course, that went bad. You need to really just have some light-hearted fun because you have nothing to lose. This is only the second date, so if things do not work out then it will be back to the dating site or dating app.

What to do

You need to keep the second date simple and fun. Plan to do something active and engaging that might also offer you both a way to get to know each other better. I took my wife out to a really unique bookstore in German Village where I used to live.

The bookstore has 32 rooms and is in an old historic house that was turned into a book loft.  We had so much fun hitting all the rooms and looking at the different books. You get to know a lot about a person when you take a look at what areas of the bookstore they like. We got something to eat after the book loft so the night was fun.


Here are ideas of fun things you can do on a second date.

  • Local festival or fair
  • Unique places in your city like the book loft
  • Sports event like MLS or baseball if you both like sports
  • Visit a winery local to you
  • Comedy club
  • Many cities have areas where you can walk around different unique shops maybe try that
  • Go for a hike on a nature trail
  • Go paddleboarding
  • You can rent jet skis on a lake or if you are by the ocean
  • Visit a museum
  • Bookstore

There are so many unique and active things to do wherever you live, you just need to have some imagination. Whatever you plan, you need to make sure your date has some interest in the same activity. Also, make sure your date has the ability to do what is needed for the date.

Be yourself

You want to be a little more open about yourself on the second date. The one thing you do not want to do it to get too deep too quickly. Whatever you do, don’t mention your past girlfriend or past boyfriend. I would not be negative or talk about anything negative. The date should be fun with the mood being light. You can reveal some cool things that the date may not know about you, but still, keep some things in reserve.

Listen and remember

Hopefully, you did not meet your date on a drunken excursion. You need to remember what they talked to you about from the first date. If you can remember the important things that were said it will help you score points when you bring it up.

The date may have mentioned they were looking at going to grad school. You can ask if they were still thinking about it and when would they plan to go.

If you have difficulty remembering things, just write some notes down at the end of the night about the details of the date and what you talked about. I have a note-taking app on my phone too which I put information and names of people so I can remember next time I see them.


Just like the first date, you need to ask questions. The more questions you ask the more they feel you are interested in them. People love to talk about themselves and asking questions gives them that chance. You can ask some funny questions to help break the ice. Here is an article we wrote top 36 funny first date questions. You can ask these questions anytime throughout the dating process, so it does not have to be the first date.

The more questions you ask the more material you will need to remember. If your memory is poor make sure you only ask questions of things you can easily remember. It’s the second date so keep the questions light for example:

  • Where did you grow up?
  • If you had one wish what would it be?
  • What is your favorite thing to do?
  • Do you have any siblings?

Just keep things fun and light when talking. They will probably ask you some questions back so if it gets serious try to lighten things up with some fun questions.

When you’re on a date, do not look at your phone unless you must. Checking your phone all the time and not focusing on your date is rude and will come off as though you aren’t interested in the person at all. You should not check your phone or text during the date because if you do, you can kiss the 3rd date goodbye. Nobody wants to date someone who has more interest in a phone than in them.


You both want to feel good on a date so make sure the compliments flow if the chemistry is working. A guy might say things like, “You have really toned legs,” or you could say, “You are very easy to talk to.”  The women may say things like, “I love how witty you are,” or she may say, “You have a great smile.” Just the littlest things help make the date special and will help form a stronger connection. Every date builds on the previous date until you are very comfortable with each other.

Having fun


Along with compliments come some ramped up flirting. The compliments will bring about some flirting so have fun. If you like this person then let them know it in subtle ways. Use compliments to help guide the conversation. If you are somewhere crowded you can brush up against each other. Let’s say you go to a club and they have dancing, what a perfect opportunity to start flirting. Dancing is so intimate there is no way to avoid a physical connection.

If you never learned how to dance or you feel uncomfortable in a club scene, then try to avoid a dance club and steer the date to something else. Maybe do putt-putt which you may laugh at but it is outside, fun and you can get close showing her or him the best way to putt.


You need to be safe anytime dating new people. This is more so for women than for men. Here are some safety tips for women when dating someone new.

  • Drive or meet them at the place for the date
  • Never have them pick you up at your home or anywhere
  • Carry mace with you on the date
  • Do not share your address on the second date
  • Do not drink heavily and rely on him to take you home or worse take you to his house
  • Have an exit plan if the date goes badly
  • Check your date out on Google
  • You can also check out your date on social media

Do not stalk them

You do not want to send a friend request to them after the first date or the second date. There is no reason to friend them on Facebook then send 10 messages after the date. They are going to think you are crazy and probably never call you again. Chill on social media when you first start dating someone. You do not want to look desperate or creepy on social media. You can friend each other if you both agree but just leave it at that until you can see how the dating progresses.

You also do not want to go text crazy on them. Just a simple text here or there will work till the next date. No need to make someone think you are a stalker. Stalking is bad in today’s world.

What do they like?

On the second date, you do not know everything about the person, but hopefully, you know just enough to impress. You may know that they do not like certain foods based on the first date. You want to avoid those restaurants if going to get food on the second date.

If your date does not like water activities, then do not schedule a jet ski or paddleboarding activity. You really need to pay attention to your date so you can plan the second date accordingly.

A first date is a good place to at least find out what they like and do not like. This will make all future dates easier to plan.

1st base

If the chemistry is right for both people then doing some kissing on the second date is a wonderful way to connect. There are signals you can watch to see if the timing and mood are right.  The end of the date is often perfect timing for a kiss. The end of the night kiss will tell you if they are interested in continuing to date. If your date back aways or does not show interest in a kiss, then they may be not as interested in you as you are with them. Just see how it all plays out after the date.

Another option for a physical connection is holding hands. Perhaps while you’re walking somewhere on your date reaching out to hold hands is a simple gesture that involves connecting in a physical way and can be a wonderful way to express attraction too.

Sex on the second date is not a wise idea. You should stick to a kiss. (If you are not interested in this person for future dates, simply say goodbye and move on.) Having sex on the second date will complicate the relationship because you have not gotten to know each other well enough. If you are just dating to have sex, then doing it the second date may be an acceptable decision for you both.

Third date

Things are looking good after the second date so you ask for a third date at the end of the night. If you are not sure about going out again, leave a window to plan the next date and just say you will text your date in the next few days. In the next few days, you can decide if you want to go on a third date. When you feel confident in your decision, go ahead and reach out to plan your third date.

Love languages

It might be too early to figure this out but it never hurts. In Gary Chapman’s book, “The Five Love Languages“, he describes 5 different ways we express and communicate love. It’s an interesting and useful perspective for any relationship and it might be helpful for you to consider as you continue forward on your third date. Perhaps you can figure out which love language you use most and maybe you can identify which one best fits your date. Knowing this will help you in the future if you continue with your relationship.

Here are the basic 5 love languages

  • Words of Affirmation – This language uses words to affirm other people
  • Acts of Service – Action speaks louder than words for these people
  • Receiving Gifts – Some people like getting a gift
  • Quality Time – This is about giving the one you love your undivided attention
  • Physical Touch – Touching them is how this person feels deeply loved


The second date should be fun but if it is not perfect don’t be discouraged. The third date may be a charm if you just go out a few more times. I know this because my wife said our second date was not that great but the third date was awesome.

Hope these tips help you when dating. This is all about meeting new people and having fun. Enjoy the time out with someone new.

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