• IJL Team Member Annalee

5 Ways to Score that Second Date

We all know that feeling when you want to nail that second date. That’s part of the anticipatory anxiety of going out on a first date. Will they like me? What if it’s awkward? What if I like them and they don’t like me? And before you know it you have already given up before you started. Being a good dater is all about confidence and a willingness to be open to any experience. Below are five full proof steps to getting that second date and becoming an expert at dating.

Spend More Time Asking Questions

No one enjoys being in the company of someone who incessantly talks without a breath. The majority of my professional career as a matchmaker, this is one of the most discussed feedback I have with clients. Even if you aren’t a Chatty Cathy, sometimes when people are nervous they have a tendency to fill in with unnecessary “filler conversation.” Pause, breathe, take a sip of your wine and ask your date a question. Don’t be afraid to probe with deeper questions such as “what is your philosophy in life?” or “what are you most thankful for in your life?” People enjoy light conversation, but they also want to know you are capable of going to that deeper level that we all long for in a relationship.

Ditch the Business Clothes

This might seem obvious, but you might not realize that you’re not dressing the part. A lot of professionals have a tough time leaving the business at the office and bringing their fun side to a date. If you’re a man, wear nice slacks and a button down. If you’re a woman, wear a dress or a skirt with a top that is flirty. Dating can be fun! Don’t be afraid to up the sex appeal on a date. If either party finds they have sex appeal, they get a second date. Everything in moderation of course, but leave the business clothes at home and enjoy being yourself.

Don’t Be a Whiner

Is it hot in the restaurant? Ignore it. Is the waiter slow? Don’t mention it. Was it a bad day at work? Keep that to yourself to discuss with a friend later. You want to present your best self and complaining, even if it is legitimate, gives a subliminal message to your date that you are discontented and negative.

Give a Compliment

Make your date feel good, be sincere, Perhaps look at something he/she is wearing or doing and tell them how much you like it. Everyone wants to know their potential partner will be loving and complimentary. Often, when one person opens the door to flirtation through a sincere compliment, the chemistry follows even if you aren’t typically attracted to that person. Tell them “You look beautiful” or “You have amazing hair” or “You have the most striking eyes.” Be honest because false flattery will not work! I had a client once tell me she went on a date with a guy who wasn’t her type, however he said something that turned the date around: “You have the most beautiful eyes, I actually got lost in them for a second.” They are happily in a long-term relationship. Don’t be afraid to give a compliment, good things will follow.

Give Chemistry a Second Chance

Now, if you’re on the flip side of this situation and you’re unsure if you want to go out again, read on. I tell my clients the following all the time and because of that push I have produced many happy relationships: If you had an enjoyable time, friendly conversation, laughed and didn’t have a terrible experience, but were unsure about chemistry… go out again. If you go back to section four, you’ll see that perhaps the flirtation can be better next time or refer to section two and up the sex appeal. Your date might have been nervous or had a terrible day, there are variety of reasons that your date might not have been themselves. Most importantly, remember chemistry grows over time. From my experience, people who have this “cosmic” connection from day one and jump in head first rarely have a sustainable relationship. Go out again, get a no pressure drink and give love a chance.


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