Third Date Milestone: 6 Things to Discuss on Your Third Date

Yeah. We’re pretty sure that you’ve heard of the “three date rule” before. There are a lot of people who set that as a personal milestone for when they’re ready to engage in sexual intimacy with the person they are dating.

However, this article isn’t about that. At least not specifically.

When it comes to that unofficial rule, we will agree with it in the sense that if you’ve gone on a second date with someone, that is usually an indication that both of you are pretty interested in one another (that’s why matchmaking companies like Tawkify are proud of the fact that over 80 percent of their clients end up going on a second date with one another). And if the second date goes well, a third date sends the message that something very promising is happening.

That’s why if you’re preparing to go on a second date with someone, it’s important that you’re intentional about taking things up a notch.

We’re not saying that it’s time to start picking out engagement rings and baby names. But it is a good idea to bring up a few topics to see if this could be the relationship that you’ve always been looking for or if you’d probably be better off being just friends. (Good friends but just friends nonetheless.)

So, what are the things that you should be open to discussing on your third date? Here’s our “six list”:

Are you looking to be in a relationship? You’d be surprised how many people have absolutely no problem casually dating (multiple people, we might add) for months on end without it going any further than that. So yes, on your third date, you are well within your rights to ask your date if they’re interested in having a relationship. Just remember that there is no right or wrong answer to this question. You’re simply asking so that you can gain an understanding about if they want what you do.

When’s the last time you were in a relationship? If you can avoid dating someone who is on the rebound, we highly recommend it. The only way to know that is by asking your date about the last time they were in a relationship. If it's only been a few weeks since their last break-up, that doesn’t automatically mean that you should stop seeing them. What it does mean, though, is that you should definitely take things slower both emotionally and sexually. A break-up is like a wound that needs time to heal. Plus, people are usually not able to make the best decisions about what’s right for them in a new relationship until they’ve resolved an old (the last) one.

Do you have time for a relationship? Even if the person you’re dating wants to be in a relationship, that doesn’t always mean that they have the kind of time to invest in the type of one that you may want. For instance, if you desire to go out on dates every weekend and they work a second job, that, in time, could prove to be a bit frustrating. Discussing one another’s schedules is a courteous thing to do. It will also help you to gain a greater understanding of what you can/should expect in the future.

Who are the closest people to you? You can find out a lot about a person by listening to them talk to you about their family members and friends. People whose parents are still happily married may help to give you a sense of stability. People who’ve had the same best friend since high school may speak to their level of loyalty. People who are close to their siblings might help you to feel like they are sensitive and embrace family life. Yep. It’s always a good idea to know about the person you’re dating’s other relationships. It can help you to learn more about them and that’s essential.

What are your sexual expectations? Some folks might think this is being too abrupt, but sex is a part of a relationship. Besides, if someone is trying to spend more and more time with you, this means that they want to get closer to you. This means that you should know just how close--and when. Can you just imagine what it would be like for a person who wants to be abstinent until marriage to try and maintain a relationship with someone who thinks that sex less than 2-3 times per week is a dry spell? This doesn’t mean that you have to say “So, are you looking to have sex tonight?” It simply means that once you hit three dates, it’s OK to share your personal stance on sex and the purpose that it serves for you.

What new things do you want to try? Once you’ve gotten some of the heavier things out of the way, don’t forget to ask about what they’d like to do (preferably with you) that they’ve never done before. One of the best things about a budding relationship is it gives you the opportunity to not only experience a new individual but hopefully associate them with trying some new things too. Dinner and a movie is so cliché and by the third date, you’ve probably already done it. On the fourth date, do something fun, exciting and unique. It’s a surefire way to take your dating relationship to another level. In an enjoyable, lighthearted and yet productive kind of way.

6 Things to Bring Up on Your Second Date

So, you made it to your second date, eh? Although you might not think that you’ve accomplished a major feat, a lot of matchmaking companies can personally vouch for the fact that if you’ve had a successful first date, that is something to be pretty happy about. Not only does it mean that you’ve obviously made a great first impression; a second date also shows signs of a connection being established too.

Now that all of the initial introductions have been made, it’s time to scratch a bit beneath the surface. After all, dating is not just about hanging out with another individual (you can do that with your friends!). Dating is about investing time into another person in order to see if there is a potential relationship that can come from it.

That’s why, before heading out on your second date, it’s a good idea to have a few questions in mind. Ones that can help you to see if this is the kind of person you want to get to know better on a romantic level, is the kind of person who should be no more than a friend or is the kind of person where the second date also needs to be the final date. (Here’s hoping for Door #1, by the way!)

What are you looking for? Off top, this question might appear to be “What are you looking for in a person?” but actually we mean “What are you looking for a relationship?” Some of you might have caught the movie That Awkward Moment (Zac Efron, Miles Teller, Michael B. Jordan) where in the beginning, Zac’s character had a girl break up with him only for him to say to himself “I had no idea we were actually in a relationship.” You know the drill, perception is reality and you don’t want to spend six months thinking that you’re heading towards something serious while the person you’re seeing is taking the casual approach. Knowing that you both want the same kind of relationship helps to set a firm foundation.

What are you passionate about? A common question that folks tend to ask on dates is “So, what do you do for a living?” But basically all of us know at least one person who has a job but is not pursuing their actual passion. Two great things can come from asking someone this question: One, you can gain some pretty profound insight into their loves and interests. Secondly, most individuals find this to be a thoughtful approach to a conversation. You’ll get at least a couple of smiles and twinkle of the eyes with this question. Guaranteed.

What are some of your favorite things? Everyone has favorite things. Favorite songs, favorite movies, favorite colors and quotes…favorite holidays and activities. This question helps you to learn an intimate side of the person you are on a date with without being too invasive. Plus, should the date go beyond a second one, you’ll have an idea of what they like to do and see. It can actually make planning future dates a lot easier.

What are your pet peeves? You’d be amazed how many married couples are considering divorce court right at this very moment because “the little things” have suddenly become pretty big ones. Asking your date what their pet peeves are is basically a lighthearted kind of way of asking them what gets on their last nerve. Is it people who eat and talk at the same time? Is it people who text while at the table? Maybe it’s individuals who go on and on about themselves. The sooner you know theirs and they know yours, the more proactive you both can be when it comes to avoiding these little irritants when you’re together.

What’s your schedule like? There are a lot of people who really like each other, but are not able to spend as much time together as they would like due to conflicting schedules. If your date has a day job while you work at night or both of you have weekend gigs, that could ultimately prove to be pretty frustrating. Finding out when and how to make the dating thing happen is paramount.

What would you like to do next time? Say that you were to find a date through a professional matchmaking company like Tawkify. If you were to ask a matchmaker about another question that you should ask on a second date, if the date went well, as it’s coming to an end, don’t be shy about asking what they would like to do the next time. It shows interest and also initiative. These are both big pluses when it comes to letting your date know that you’d like to get to know them even better. That you want another date. And another. And another.

Follow-up Etiquette: 5 Things to Do After a Great First Date

A wise man once said that the way something starts often is a prediction of how it will continue to be. Perhaps that’s why so many of us single folks long for great first dates. There really is nothing like meeting up with someone, having an immediate chemistry, going to a place that both of you like and then never wanting the date to end. *sigh*

There are certainly all kinds of scenarios that can lead to a great first date (meeting someone on your own, using an online dating service, testing out a matchmaking company like Tawkify). Unfortunately though, there are a lot of people who end up being so caught up in the euphoria of the experience that they don’t take advantage of the crucial and fragile time following their first date. They overlook things that they should do in order to insure that a second (and hopefully second, third and fourth) date will soon follow.

So, just what is the follow-up etiquette after an amazing first date? Good question. Although there are all kinds of things that you could do, here are five that should definitely go on the very top of your list.

Mention a second date---on the first date. If you’re having a great time, what’s the point in keeping that to yourself? Towards the end of the date, it’s perfectly fine (encouraged even) to say “I hope we can do this again sometime” or “Next time let’s try going to so-and-so.” That let’s your date know that they’re definitely on your radar; that going on a second date is something that you’re definitely interested in doing.

Get their contact information. Does that sound obvious? Yeah, you’d be surprised how many people miss the obvious sometimes. Being that a lot of us are much more tech-savvy than the generations before us, not everyone talks on the phone before going on a first date. Say for instance that you met via one of your social media accounts and everything was via email. Once you’ve met and had a great date, it’s then time to take things up a notch. Getting each other’s phone numbers or asking for another way to get in contact with your date sends the message that you want to get to know them better. And them giving the info to you lets you know that they feel the same way.

Don’t be physically closed off. A professional matchmaker is probably going to recommend that you pump the brakes when it comes to physical intimacy. No matter how good a first date is, you still need more time to get to know someone better before giving up the goods. But that doesn’t mean there’s something wrong with extending a hug or kiss on the cheek. It helps to break down any potential barriers. It’s a way of conveying warmth and interest without overdoing it.

Leave a message or send a text that same day. OK, all of that “I don’t want to seem too eager” crap usually tends to backfire. No one is saying to call them 10 times on your way home (that’s a stalker and no one likes them). However, it’s both thoughtful and proactive (proactive is big with the ladies, guys) to leave a voice mail or shoot a text that says “I had a great time on our date. I’m looking forward to seeing you again.” It only takes a second and it’s time well spent.

Call within the week. Another mistake that first daters make? Playing the perpetual waiting game. You know: “He should call me first” or “If she’s interested, she’ll call.” Stop it! Just pick up the phone and call. If they’re still interested, you’re that much closer to your second date. If they’re not, well, making the call will let you know that sooner than later. This means you can---and should---move on. Either way, it didn’t take a month to find out what you needed to know. You are able to confidently take the next step in less than a week. Awesome, right? Right.

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