The Secrets Of Second Dates

Finding someone who warrants a second date doesn’t happen every day. Every date is it’s own snowflake; but like snowflakes, some of frozen, cold people. Follow these rules to maximize your success.

Rule # 1: Plan Well

Second dates can be savored as a rare pleasure of a bygone era: having fun while getting to know someone new. It’s your chance to learn more about each other and see if the chemistry is there. But nerves can still be high. To optimize conditions:

Do:

1. Make a good, simple plan– set the stage to bring out the best in the both of you.
2. Be yourself – whether she seems above or below your pay grade, you never know unless you spend time together. The more authentic you are, the more you will attract the right people in your life.
3. Pace it – plan for two to three hours. But keep the address of a nearby bar or coffee shop in your back pocket just in case it goes longer.
4. Check yourself – strike a balance between candor and civility, a.k.a. try not to over share.
5. Dress well – a second date should rate your equivalent of business casual with an ironed shirt. Nothing too fancy, but no jorts or anything. Have some respect, man!
6. Breathe – in between sentences and while she is talking.
7. Listen – as much as you talk. Split it 50/50.
8. Pay attention to your rebound status – too soon? Has it been too long? Just be present with this one person and don’t bring your baggage into this date.
9. Expectations – she may look perfect; but she’s not. Neither are you. Remember you are going to hang out with just another human being.

Rule #2: Connect Well

Now that your head is on straight, you can think about what you are going to talk about. Our world is in such a turbulent state and so many subjects seem off limits. Rather than discuss the most current outrage of the news cycle, here are some ideas for conversation:

Do:

1. Pick something she spoke about on the first date and go deeper.
2. Ask what drew her to her work and what she is passionate about? Do those two things line up? If not, why?
3. Books, sports, art and movies are always great lead-ins to deeper topics and mutual interests or a way to learn something new.
4. Religion will probably come up. Have an open mind and ask neutral questions.
5. Cats vs. dogs, pie vs. cake, pudding vs. please don’t seat me in the same room where there is pudding—these are the things that might give you all the information you ever need to make an informed decision about a person.

Don’t:

1. Talk about the colors red or blue: pills, states, food dyes. Just stay away. Although you might want to know quickly who is with you or against you.
2. Whether you are for or against, nothing gets people more riled up than talking about the The You-Know-Who in Chief. Adrenaline like that is not good for second date.
3. Get defensive. If you hit a snag, and you will because all human beings can’t agree on everything, listen with an open mind, relax your shoulders and see where you can meet conceptually, if not specifically. That said, use your common sense. If someone’s beliefs are so counter to yours, then you can politely wrap things up.

Rule #3: Reserve Well

Some guys think that if it’s really meant to be, you can take your date to Ruby Tuesday’s, split the bill and it will end happily ever after. If you are the total package, go for it. But if you are a mere mortal, you might want to choose an environment that will work in your favor. Don’t try too hard to impress, try two notches up from easy breezy. You want her to know you have good taste and that were taking her into account. Pay attention to what you both have in common from the first date, duh. i.e. don’t take her to a museum if she said she was a die hard Knicks fan. Here are a few ideas on what to do/where to go:

1. Museum – Art. You love it, you hate it, or you are intimidated by it. But it is a chance to walk around, talk, and gives you subject matter to talk about. If you are unsure of her taste, some cities have craft, architecture or history museums.
2. Outdoor spaces – walking in the park, highline or any public space with greenery can bring you to a new space within a space. Don’t go anywhere too bramble-y. And have an eating plan afterward, no matter how small. Even If you buy her a pretzel or an ice cream during.
3. Restaurant – Old faithful. Sitting across from each other is always a good idea, seeing if your tastes line up, checking each other’s manners, drinking habits and how both of you treat serving staff reveals a lot.
4. Botanical gardens or zoos can be fun.
5. Check out a comedy show and have a comedian do the work for you.
6. Get tickets to see a band, or a jazz show and have a drink before or after.
7. Roller skating or ice skating—if you feel confident enough to not fall over.
8. Rooftop bars can set the stage for great conversation. Sometimes if it’s too loud, you have to lean in closely to hear each other, which is not terrible on a second date.
9. Pool or Bowling – always fun and not too competitive.

Don’t:

1. Do anything in an enclosed space for too long: boating, train rides, exploring new neighborhoods after a ferry ride. If the chemistry is not working between you, it can compound the discomfort with no exit plan for either person.
2. Go to a movie. Too close, too quiet, too dark, too soon. Too many opinions afterward.
3. Netflix and Chill. Not saying don’t Netflix and Chill. Go for it, have fun. But it’s not an actual second date. Enough said. Not saying it couldn’t work out long term. It’s just not in this category.
4. Go to a burlesque or a risqué show. For those of you who have not seen The Graduate or Taxi Driver, just don’t. Unless you are on a date with a sex blogger, columnist or someone in the lifestyle. And you found that out in the first date.
5. Picnic. Too soon, too intimate, perhaps too much grass and dirt.

Dicey: You should be certain you share these interests before you proceed

1. Amusement Park – Rollercoasters are like cilantro: it’s a love or hate thing. If you are certain you’re both into it, then get two tickets. Unless it’s an open boardwalk with those games, don’t.
2. Food festivals with a specific theme: Speaking of cilantro: oyster week? Hot chili festival? National Doughnut day? Everybody is pretty specific about food, whether it’s allergies, eating disorders or taste. You don’t want to put anyone on the spot or have anyone yuck your yum so early on.
3. Wine Tastings, biergartens – people don’t always want to disclose their relationship to alcohol. You don’t want to have to play  “Whose Uncle Is An Alcoholic?” in the middle of the second date.
4. Baseball Game: America’s past time is sloooow. Even sitting in the middle sections won’t break the bank. There is a lot of down time to chat and fun food to eat, if you like that kind of thing.  But it can be boring and if you don’t have flow going, it can add awkward to boring.
5. Any activity that has you shedding clothes like swimming or going to the beach.  
6. Anything too competitive or potentially painful: paintball, tennis, basketball.

Rule #4: Kiss Well 

Should you kiss on a second date? Yes: If you are both feeling it, pucker up. But set aside expectations, scenarios from plays, books or movies that you carry around in your head. To know if you should kiss on the second date is something you will find out during the date, because it will be obvious.

How do you know? There is a ton of scientific evidence about feet pointing toward you, dilated pupils, flared nostrils and twirled hair. But these can be hard to see if you are in a dark space or sitting down. And if you are getting nervous, feeling distracted by your desire to kiss her, you’re not going pause to ask her if you can check to if her pulse is quickening.

You might be a little confused about how to proceed. Many women love a man who takes charge, as long as he is reading her cues correctly. Here are some clear signs she wants to kiss:

1. Genuinely laughing at your jokes—especially the dumb ones.
2. Relaxed, open body language.
3. Leaning in.
4. Asking you questions to extend the conversation.
5. Increased quick banter.
6. Getting closer to you, physically.
7. Looking deeply in your eyes.
8. Arm or leg touching.
9. Licking her lips.
10. Looking up from her down turned head.
11. Twirling her hair, apparently.

But the best way to know if she wants a kiss is to say, “Hey, I really want to kiss you right now.” That is a huge turn on for a woman who feels the same way. And if she doesn’t, you will see the obvious recoil or she will kindly decline.

The more she leans toward you, verbally and non-verbally, that implies yes. Congratulations! Even if she takes a pass, it doesn’t mean the date wasn’t successful. If your conversation is still in flow and she is extending things, she is probably still interested. She might need to get to know you a little better. That means that you did a great job with this second date. Kiss or no kiss, tip toe forward, if you are feeling it, and ask her out on the 3rd date.

— Kim Thompson