A Guide to Nail Your Third Date

Dating 101
13 Sep 2023
12 min read
How to Have a Perfect Third Date: 6 Tips and 7 Ideas

There’s that old saying, “The third time is a charm.” Usually, it refers to someone trying something and then gaining success. There’s also that saying, “Three strikes, you’re out.” Both of these can apply to a third date, depending on how it goes.

How It Started – How It’s Going

Mostly, that first date was really just an introduction. You met up, had lunch, dinner, or a few drinks, shared general information, and probably kept the conversation casual. After all, at least in a dating environment, you are total strangers at this point.

If things went pretty well, you set up a second date. Now, you may have done something that both of you agreed would be fun – these things you discussed on the first date. And you both had a good time, probably sharing more information about yourselves but not necessarily intimate stuff.

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You may have talked about your families over dinner; maybe went rock climbing or decided to play mini golf. All in all, you both felt some attraction and maybe engaged in a little PDA – a hug, a parting kiss, for example. But conversation topics were still pretty casual.

So, it’s time for the third date. You’ve shared date ideas for this event and mutually decided on a place and time. If you feel comfortable enough, one of you might have picked the other up so you could drive together. Here is where things get a little more complicated and intimate – and how to navigate all the inconveniences.

What to Expect on a Third Date

Here is where some of the “rubber meets the road.” It’s time to get down to the business of more intimate conversations, so you both can see if there is enough compatibility to move forward. If you feel unsure of what to expect and how to behave, try to access our app and chat with other people about how their relationships progressed during the first few dates.

You might get a closely related story to yours or at least some experiences that will help you prepare.

5 Main Questions to Ask

“Listen carefully to their answers. Don’t just hear what you want or mold their responses to align with your ideal match. Actually listen and determine if this is a person that is actually worth investing your time. The third date is where we’re telling each other something about the type of partner we could be – listen when someone tells you who they are, that isn’t changing.”

Erica Cramer, dating and relationship specialist

Here are some of the most important questions to ask:

  1. Are they looking for a long-term relationship or just casual dating?
  2. What are their political and spiritual beliefs?
  3. What are their goals for career and partnership?
  4. How did their last relationship end?
  5. What are the most important qualities that they want in a partner?

If you have any deal-breakers, this is the time to learn about them. There is no point in becoming romantically and emotionally attached to someone if you know it will not turn into the relationship you are looking for.

If this potential partner avoids answering these questions, consider that a red flag. They may just be a serial dater who has no intention of spending time really getting to know you or for you to know them. They are not worth pursuing – no future here.

Related reading: The Serial Dater – A Special Breed

And you must share your answers to the same questions you ask. Be certain that you are honest and authentic. There is no point in putting on any type of façade just to be more attractive – who you really are will eventually come out anyway.

Third date activities

Plenty of Things to Do on a Third Date

There are no best third date ideas because they depend upon what you have discussed and decided would be fun as you get to know each other more. A third date can range from anything physically active to something less rigorous – a concert, cooking a meal together, a dinner theatre, an evening river cruise – any date idea that you both know you will enjoy. We’ll list our favorite ideas in a couple of sections below.

The point is to have a meaningful and fun way to spend time together but also to delve more deeply into what each of you is all about. Those deeper convos will probably not happen while you are rock climbing or at a concert – but if you go for such active third-date ideas, include some time afterward in a quiet, more intimate setting for those questions you want to ask.

Related reading: 21 Questions for a New Relationship

Will There Be Sex?

“The third date isn’t some monumental milestone that should be a make-it-or-break-it, event for a potential relationship. If you have a gut feeling one way or another about a person, listen to it. Otherwise, let yourself enjoy the ride…and a fourth yummy dinner with, at the very least, good company.”

Chloe Carmichel, a clinical psychologist

By the time that third date rolls around, sexual tension has probably built for both of you. And there is something commonly called the “third date rule.” If enough sexual tension has built up, having sex is probably a good third-date idea.

Obviously, this is not a hard and fast “rule.” Every couple is different. So you will need to get a gut feeling about how things are progressing. Have you been calling and texting between dates? Do those calls and texts have sexual hints or overtones? If so, you may want to be prepared for this real possibility.

Related reading: Relationship Bases: How Baseball and Sex Are Connected

How to prepare yourself for the sex opportunity:

  • Be certain you are ready: Do the needed emotional and romantic preparation. If you’re not, and your date proposes it, you need to be honest and say you are not ready yet. They will respect your feelings if they are interested in a relationship with you.
  • Come prepared: Bring the right supplies and equipment – condoms, lube, makeup remover, your best underwear, etc., and a change of clothes if you spend the night together.
  • Consider the alternatives: Have an after-sex and exit plan if you won’t be spending the night together. Don’t assume that the aftermath will just happen naturally, even though it might.

There is no set timeline – whatever the two of you decide is right for you is right. It might be the fourth date or beyond. But there is more to a third date than just deep conversation and sex. The dating game includes some other aspects too. Like any other you had and will have, this date should be meaningful and enjoyable.

The main third date rule is to enjoy it to the fullest

6 Tips to Make Your Third Date the Best Ever

Your first two dates are a big deal because you decide the prospects for continued dating with this new partner. But the third date matters because it’s your chance to learn if you are on the same page regarding the important things in your life and if there could be a future with this person. You need to show your true self and hope they do the same.

This date also matters for some other things – sense of humor, compatibility in leisure activities, importance of together time and apart time when you need a break, sense of adventure, etc. So here are some third date tips that should reveal more about a potential relationship prospect.

1. Show Affection

You can choose both physical and verbal to do that. Grab their hand as you are walking together; sit close to them; share hugs and kisses. And don’t forget the importance of what you say.

While it’s time for the “I love you” declaration, don’t hesitate to make other comments that show how you feel:

  • “I always feel so good when I’m with you”
  • “You have a way of making me happy just being around you”
  • “I’m so glad you’ve entered my life”

Words matter, and people tend to hold back on them for fear of their date’s reaction. So be genuine and show the real you with your feelings.

You don’t have to come on too strong to do that. And you can gauge your date’s reaction pretty quickly.

Related reading: Is Love at First Sight Real?

2. Reveal Your Fun Side

What do you do for fun in your own life? What does the person you are dating do for fun?

Ask them if you don’t yet know. Suppose you love to sing karaoke, but they like to dance. Suggest that date three include these two things. You want this potential relationship to see that you have a fun side and want to see theirs too.

You don’t have to be on your best behavior like on that first date. The point is this: try to combine two things you do for fun on that third one. Decide together.

3. Keep Your Emotions Under Control

Usually, a third date means that people are thinking seriously about relationships. And you may be feeling really emotionally attached already. Use your head now, as well as your heart. This is not the time to profess your love. Take a deep breath and wait.

This is one of those important third date tips. Even if the date ends in sex, do not let your emotions take control, and start professing love and a permanent future together. Your dating relationship may not be there yet at all, and you risk turning them off because you are moving too fast. Of course, express total enjoyment of the event and show plenty of affection, but leave it at that.

Wait until at least the next date or when they begin to get emotional about their feelings for you too.

4. Be Mindful of How They Treat Others

Once three dates are under your belt, you should know how they treat others in various environments. If you are driving with them, how do they respond to the driving mistakes of others? If you are in a restaurant with an issue, how do they treat the wait staff?

By date number three, you should have a pretty good idea. You should expect that your date treats others, especially service workers, with respect and empathy. If not, you may want to re-think whether they are the right relationship.

5. Don’t Be Possessive

When relationships grow, it’s easy to begin to think that the person you are with is “all yours.”

Suppose you encounter some friends of theirs on your night out. Of course, you expect them to introduce you. At the same time, you may see that they give these friends hugs and other expressions of affection. Some of them may be with members of the opposite sex.

Use your head. These are close friends, and they have a longer history with your date than you do. If you move in too fast to “stake your claim,” you may “turn off” their friends and them as well.

Related reading: How To Maintain Your Individuality While In a Relationship

Stay cool. Put on your charm and receive their friends with grace. Express your pleasure in meeting them and make every effort to be genuine about that. Don’t let your jealousy or possessiveness show in words or actions. This person had a life before they met you. Accept that graciously.

6. Respecting Boundaries is Critical

You have boundaries. So does this new person in your life. On the third date, these should be made clear and should be a part of your third date with this person. Both of you need to feel comfortable with one another’s boundaries and be prepared to honor them throughout the date.

Perhaps emotional boundaries should not be crossed yet – past relationships, for example. There may be physical boundaries related to sex. Again, these must be honored. There is time for these as the relationship unfolds. That may happen during this third date, and it may not.

Regardless, you may need to think about some third date ideas that both of you will enjoy and feel comfortable with.

The best third date ideas

7 Third Date Ideas

So, your third date should be one that both of you will find fun and enjoyable. It doesn’t have to be extravagant, by any means. There are plenty of options:

  1. Movie night: This can be at either your places or a theatre. Pick a movie together and spend time talking about it afterwards. What happens then is up to you two.
  2. Cook a meal together: Decide on the menu, shop for the ingredients together, and then go to either of your places. There will plenty of time to talk while you cook, eat and cleanup.
  3. Wine or beer tasting event: What better way to relax and engage in some great conversation.
  4. Active sport together: If you both are physically active and into the outdoors, go hiking, camping, fishing, water or snow skiing, swimming, or any other activity you both enjoy.
  5. Visit an escape room: Choose a theme and make that reservation. Now, this is normally an activity for a group rather than a couple, but if you are ready to have your squeeze meet a few friends, you can each invite another couple to go with.
  6. Go to a sporting event: If you are both into a specific sport, have at it. Get those tickets and whoop it up for your team.
  7. Play the questions game: A host of these games are available online since third dates are an opportunity to gain more insights into one another. Find a place where you can be alone – maybe at one of your places, along with drinks and snacks. Begin with the less intrusive questions and work up to the more intimate ones. If you get or give a question that causes discomfort, just move on. At any rate, you’ll get to know each other a lot more.

Now, many of these third dates won’t give you a lot of time to talk, but you can spend time afterward at a more intimate place for “debriefing” and allow yourselves to get to know each other better.

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That Third Date …Many Possibilities

If you are ready to go onto a third date with someone, you know two things. The first two dates obviously went well, and you are ready to explore the potential of a serious relationship. And so, that third date may involve a variety options. Your job is to help choose the venue and the activity, to decide how much you want to know about your new squeeze and reveal to them, and, of course, how physical you plan to be. There is no magic number of dates that will let you know if this is The One. Take these tips, and grow the relationship on your own timeline.

Dating Tips Author
Shelly Standford
After a devastating relationship breakup, I threw myself into the dating scene by registering on Hily. I had over 100 dates - some absolute disasters, some pretty average, and some that were actually great. So many stories to tell and insights to share with you guys!

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