Anatomy of a true second date

A first date is takeoff — your seatback is in the upright position, your tray table is stowed, you’ve buckled your seatbelt and are listening intently to make sure that the engines are on full throttle. A second date is climbing to cruising altitude. You’re on the way to your destination. You’re up in the air. You hope the pilot didn’t have a martini with her lunch, the flight attendant didn’t have a fight with his girlfriend, and the skies are not cloudy all day. In other words, a second date is the beginning of a settling-in period. Sometimes, a second date is wishing you were there already. Mostly, it’s trying to sit back, relax, and enjoy the flight. Whereas your first date is about fantasy — getting your hair done, being on your best behavior, and looking at your date through rose-colored glasses — your second date is the beginning of reality. You let your hair down a bit; you reveal the real — or realer — you; and you see your date through a magnifying glass, if not reading glasses.
The beauty of a second date is that real personalities can begin to emerge. Your date’s nervous laughter mellows into a great sense of humor; his or her personal résumé becomes a story of a life. Of course, the potential downside is that real personalities emerge. The date you thought was a friendly overtipper who dressed impeccably and arrived on time suddenly morphs into a flirtatious spendthrift who is narcissistic and obsessive. Oops. The important thing here is to take a second date for what it really is — namely, the next leg on your journey toward getting to know someone better. Period. On a second date, there will be more . . .

• Communicating: You move from neutral conversational territory, like census data, to more personal stuff like family history, favorite movies, the school you went to, school you go to, hometown, work life — stuff you’d put in a personal ad, stuff your next-door neighbor knows but not the ultra sensitive stuff you tell only your best friend. It’s also a good time for follow-up. You asked the opening questions on your first date; now get a bit more detail.
• Testing the compatibility waters: You want to make sure you and your date are a good fit. Your attention shifts away from how you look, act, feel, talk, eat, and slurp to the kind of person your date is.
• Probing for shared interests: While you want to express yourself on a first date, a second date is for allowing, encouraging, desiring, and listening to your date express what he or she likes and dislikes.
• Sexual innuendoes: Nothing overt, but playful flirting is good.
• Gazing into each other’s eyes: Most importantly, a second date is one step further along on the intimacy scale. It’s about stripping away the outer layer of superficiality and beginning to know your date’s soul. Few things are more intimate, or soulful, than prolonged eye contact. Don’t stare. But don’t be afraid to connect with the window to your date’s soul — the eyes.

Dates versus date-ettes

A date lasts at least three hours, is planned ahead of time, and takes place after noon in ironed clothing. A date-ette is spontaneous, can last a few minutes or an hour or two, takes place day or night, and doesn’t even require a shower. This distinction is unimportant until we begin speaking about second dates, because you have to know when the first date occurred. So first get clear in your own head what your first date really was. If it was indeed a date, good for you: Your second date is an authentic second date, and you’re right on track. If your first get-together was really a date-ette, however, then the next time you two go out, you’re really on official date number one — or maybe one and a half. That’s okay. There are no hard and fast rules here. But you may want to flip back to the chapters on first dates and take it from there if you’ve only had a date-ette. This chapter is for solid second-daters, not second-date wannabes.
First dates can be date-ettes, but second dates have to be dates. The progression flows naturally. If it doesn’t — if you keep spontaneously grabbing a bite to eat or a cup of coffee — you’re not dating. You’re hanging out.

Is It Really a Second Date?

The first date jitters are out of the way, and it’s on to date number two. Your emotions are still in a whirl but for entirely different reasons. No longer are you worried about knocking the shoes off your date with a dazzling first impression. That’s done. You did it or you didn’t. Not to worry. Even if you weren’t James Bond or Kim Basinger, you impressed your date enough to secure a second shot. Now the stakes are higher. If your first date was a rousing success, the next one better be fantastic. If date number one was so-so, date number two better score higher on the dating scale. Understandably, you’re going to feel a bit stressed as well as excited, hopeful, flattered, challenged, optimistic, and even giddy. That’s okay. Everybody feels a smorgasbord of emotions when the flicker of a potential love match has been ignited. What you want to do is chill out, keep your expectations in check, and make sure this budding relationship doesn’t burn out before it even begins. The first thing I want you to do is make sure you’re dealing with a bona fide second date. You may met your date through friends, asked him or her out to lunch, had fun, and arranged to meet again. In the imperfect world we all live in, you may have met your date in class, at a party, on the street. You said, “I’m going to Starbucks for a cappuccino. Wanna come?” He went, bought his own cup of coffee, chatted with you, had a few laughs, and gave you his phone number when you offered yours. Technically, you had a date. But who deals in technicalities when dating is concerned? In reality, you had more of a date-ette than a date.