When you’re on a second date and it’s going well, then you become more and more apt to share personal stories. If you feel comfortable letting your guard down and opening up, that’s great! Here are a few tips to help you get there:

• Make sure the other person is also sharing, and therefore is on the same page in regards to the date going well and wanting to get to know you better and allowing you to get to know them — sharing should not be one-sided
• Keep the topics positive, talk about things that make you happy
• Don’t start the “ex” or divorce/widow conversation just yet
• Stay away from relaying stories of your dating past — as funny as some of our 100hookup stories are, this is not the time to exchange them

Be a good listener; don’t interrupt and make sure to ask a few questions to show you’re giving your date your undivided attention. Bonus points for being an observant storyteller — don’t drone on and on without noticing if your audience has lost interest. You’re look for a connection; the more you share and find commonalities, the closer you will feel.

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I’m pretty sure I covered every aspect of a first date with my First Date Tips series (click on these links if you need to catch up: Go Together or Meet There, Patterns, Confirming Plans, Don’t Talk About That, Ease On In, Conversation Starters, Paying the Bill, Saying Goodbye, Post Date Follow-Up, Don’t Analyze Everything, No Expectations). But… what about the second date? Just because you chose to see each other again doesn’t mean you’re not nervous!

Second dates (and third and fourth dates) should be treated a lot like first dates in regards to having some level of formality… and with a certain amount of hesitancy. You still don’t know this person very well, you still shouldn’t be texting, and you still shouldn’t be engaging in any other social media (no Facebook friending yet!). You should still be making the effort to plan dates, and putting extra effort into getting ready, and be practicing the same conversational tips as your first date.

I’ll be going more into detail about what this all means in the coming weeks!

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After playing the 100hookup game (viewing, favorite-ing, messaging, etc), exchanging a few emails and a couple quick phone calls (to make and confirm plans), you will no doubt find yourself battling nerves before a first date no matter how confident of a person you are. Once you’ve greeted each other, sat down at the bar or table, ordered drinks and discussed the menu, there is a time when the conversation may lull — and it’s nerve-wracking!

Don’t let that moment set the tone for the date. Be prepared with topics to bring up that will be a catalyst for ongoing conversation. Of course there will be the typical biographical questions (what you do for a living, your hobbies, where you grew up, your family, etc.) but most of that was likely covered in your initial emails and phone calls, and now you need to see if you can actually carry a conversation and jive with the other person.

Think of some thought-provoking questions like:

• What do you hope your life looks like in 5/10/20 years?
• Are you where you wanted to be in life 5/10/20 years ago?
• If you could have a superpower what would it be and why?
• What is your best memory from your childhood?
• Who are 5 people, alive or dead, that you would love to talk to?

The key is to not make it sound like a rehearsed question or an interview, but rather work it in somehow… “Hey that Caitlyn Jenner interview has really made me think…” or “My 96-year-old Great Uncle just passed away and I’ve been doing some soul searching…” and so on. Current events are a great tool: “Remember that Malaysia Air plane that disappeared in the ocean? It really got me wondering about the supernatural. Do you believe in…?”

Finally, listen to your date’s answer rather than being ready to pounce with your answer or another question. A lot of conversation will likely naturally occur, but if you are mentally preparing for what you’re going to say next then you will miss out. If you are a shy person then ask a friend or relative to practice with you.

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Seriously, sometimes you need to just stop talking. It’s easy to get on to topics that are not really first date material — you’re vibe-ing and finding commonalities and having nice rapport, and it’s awkward to stop a conversation that’s flowing even when you know it’s not appropriate. So try and avoid the following topics and prevent the conversation from going there, before it gets to that point. This is a brief list:

• Exes: husbands, wives, fiances, boyfriends, girlfriends (stating when your last relationship ended/how long it lasted, how long you were married/when you got divorced is fine, just no details as to why it ended)
• Death: you just lost your grandmother, and that is awful, but it makes you sad… so perhaps don’t mention it. If you must, just don’t expand upon it
• Drama: with your job, family, friends — Do. Not. Go. There.
• Talking sh*t: whether your date knows who you’re talking about or not
• Finances: ’nuff said

Of course there are other topics that are personal to you and your story that you may not want to share. Joke about topics that are off-limits and say that you’d love to talk more about a topic if and when you’re on a future date. There are so many more positive and engaging topics you can talk about without bringing up too much about your past, or bringing in too much negativity.

It’s perfectly acceptable to briefly mention when your last break-up occurred, or what your political affiliation is, or to play hookup Geography for a minute, even if you find you have people in common you don’t like (see “talking shit” above). Make sure you are listening to the answers after you ask a question because that should organically keep the conversation going and not turn it into a job interview.

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When you are newly dating someone it is NOT the time to discuss the drama in your life, nor is it the time to whine and complain about things in your life. I’m not saying to make everything sound wonderful and perfect, but don’t turn a date negative with your stories about how your friends are fighting, or your siblings aren’t speaking to each other, or your job sucks, or… or… or…

There’s the normal vent about your computer crashing before you had a chance to back it up one last time, but spend about a minute on things like that and move on. That type of vent is something everyone can relate to and empathize with — and may even have advice to help you. If the dating turns into a serious relationship then you will have plenty of time to be the sounding board for drama!

Not everyone has a backstory, but lots of people do. Positive or negative, when to reveal that story after you begin dating someone you really like is a normal worry — especially when you have something important to divulge.

I’ve written previously about being honest and addressing a physical disability from the beginning; and I’ve written about how to discuss a divorce and/or having children in a minimal way in your profile and on a first date; but how about a backstory that isn’t visible? Are you a cancer survivor or do you suffer from depression or were you abused or were you adopted or any other background that made you who you are… but no one would necessarily know unless you told them?

This type of backstory is not one to include in your 100hookup profile, or even to bring up on a first date, but you do need to open up relatively early on. If the story is too much for your date to handle, then let them leave — clearly it’s not the right person for you and that’s why you need to reveal your story sooner rather than later. Unless it’s relevant to a conversation you are having on a first date, then save your confession for your second or third date. This does not mean that you are ashamed of your backstory, just that you want to have prospects get to know you for you, and not your story, particularly if it is a sob story.

There are certain things that are not to be shared on a first date. If it has to do with sex, drugs, or any other illicit activity, then hold off… maybe forever. Lots of things fall under the sex category, including nudity, number of partners, pornography, strippers and so on. Anything along those lines should be considered over-sharing. Drugs include both the prescription kind as well as the illegal kind. No one needs to know about that on a first date! Money, why past relationships ended, and anything having to do with drama can wait for another date.

First date topics should start with continuing the email conversations you began, which usually address your commonalities. Just let it flow naturally from there. If you find the rapport waning, then revert to asking questions from the 100hookup profile. “Remind me again where you went to school/where you grew up/what you do for a living/how many siblings you have?” Those are always easy ways to get the conversation going again.

Most first, second, and even third-date conversations follow a similar order of topics. And as people begin to open up and tell you about themselves, they tend to embellish, exaggerate, or simply make everything in their life sound pretty awesome. But no one’s life is ever so glossy and polished.

It can be difficult to know what’s the truth, the whole truth, and nothing but the truth. Somewhere in there is a half-truth, an omission, or a blatant lie… but it’s not always easy to figure out what those things are. It’s normal to want to make everything sound nice, but it can set you up for major disappointment later.

Is your date being vague in describing why his or her last relationship ended, or how successful their business is? Is there a lot of name dropping and the use of a lot of people, places and things to impress you? You may never know the full extent of the amount of the bull people spew (everyone does to some extent), and unfortunately there will be at least a few times when you find out the hard way — after you’ve fallen in love — and you’ll have to decide how important those misrepresentations are.