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For all of us 9-5’ers (but really, 9-whenever we are able to swim our way out of the piles of to-do lists that overcrowd our desk and go home), weeknights are a precious time where we are able to garner up just enough energy to plop our tushes down on the couch and fall asleep to the rumbles from the television.

Going out on dates on a weeknight have become a challenge for my exhausted, over-worked self. Just recently, I was enjoying myself on a date when I could feel my head slowly tilting to the side, longing to gracefully fall onto my plush pillow. If ever there was a time to say, “It’s not you, it’s me,” this would have been it.

I’ve found it equally as awkward as it is difficult to find the right way to end a date and call it night without making it seem like you’re uninterested, or trying to cover up mid-sentence yawns. Here’s some ways to do it.

• Do: Be perfectly upfront and honest. Say you have to wake up super early for work, as I’m sure they do as well, and explain how it’s getting a bit late. Throw in a bit of laughter and say something like, “I can’t believe we’ve been chatting for 3 hours already!” Be bold and tell them you’d love to continue this conversation, or this date, another night—maybe even on the weekend.

• Don’t: Be rude and cut them off mid-sentence and say you have to get going or stage a fake escape by having one of your friends send you an “I need your help ASAP” text message. I’m guilty of doing this once in my life and I ended up looking like a pathetic fool.

Read more from Jen Glantz at www.thethingsilearnedfrom.com

No one wants to get their heart broken, and likewise, no one wants to intentionally break anyone’s heart. That’s why many of us decide that when it’s not quite working with someone, when the stars just aren’t lining up, instead of getting fireworks in our belly, we get indigestion — it’s easy for us to tip toe around the brutally honest truth and try to hide our true feelings behind polite one-liners that we hope will do the dirty work for us:

• It’s not you, it’s me.
• I’m terribly busy and this really isn’t a good time.
• I’ve started really, seriously, seeing someone else.

The only thing worse than throwing one of these sentences onto a person you don’t want to see again is having them not get the hint. There’s no trick when it comes to figuring out if someone is not interested in you, it’s just being able to accept the truth. Follow their words, but ultimately trust your gut.

Do: Follow up with someone you enjoyed going out with on a date. See how they are throughout the week, then ask them if they’d like to go out again. If you are feeling unsure whether or not someone would like to see you again… or you are getting too many wish-washy responses from them, pick up on their signs and swallow their constant “I can’t” as an indication that, unfortunately, they are not feeling this (Don’t fret, there are plenty of other people out there that will have goo goo eyes for you)!

Don’t: Be overly persistent or pushy with your follow-ups. Don’t sign off your text messages or emails with “Please go out with me one more time, I promise you’ll be impressed” or threaten them with a “I won’t give up on asking you out.” If you’re feeling that you are the only one who is excited to see you again, don’t force it. Bow out gracefully and search for someone else who will be your true match.

The best part about being on 100hookup is having other friends who are on it as well and can fully understand what you’re talking about when you start to vent and run away wildly into an online dating story.

The other day my friend was telling me about how she met this guy on 100hookup and things were going smoothly. I nodded my head in happiness and sighed with a bit of jealousy, hoping that one day soon I could say the same. But then she told me after each date she texts guys saying, “Thank you” and that she “had a lot of fun.”

My eyebrows immediately raised and I let out a giant, “WHAT!” I had always thought it to be girl code that you wait until the guy texts you first after the date. My friend, who is a couple of years younger than me (but obviously a few years wiser), told me no way—that is how you lose them!

She couldn’t be more right.

Do:

• Tell someone you had a good time with them — both in person and then after — via a thoughtful text or a quick phone call. There are so many anxieties that cross our minds before, during and after dates. Alleviate the tension, the guessing and the what if’s through positive affirmations — if you are indeed having positive feelings.

Don’t:

• Hold back. You took the giant step of putting yourself out there, and then, you took an even bigger step by going on blind dates with people you’ve briefly conversed with by chomping down sentences on your keyboard. If you promise yourself not to hold back, to break some of those age old rules, you will have nothing to lose.

Read more advice from Jen Glantz here.

Why is this day different from any other day? A day where love birds bat their eyelashes on top of one another and gallivant around providing an ungodly amount of PDA that’s seriously crowding your comfort zone.

You may find yourself asking that Passover-like question this week as the glimmering red tissue paper and stuffed bears haunt you as you’re just trying to make it through another Valentine’s Day — alone. But it doesn’t have to be that way. For us, the ones who are on a holy quest to find a mensch that can warm their frosty winter heart (as much as a quick slice of pizza can), it’s day that warrants us to feel special.

I’ve spent Valentine’s Day squeezing teddy bears filled with chocolate given to me by my parents, on first dates at fast food restaurants, over a glass of Pinot with good friends, and even, occasionally, face-to-face with some ice cream cake while turning the pages of a book of Neruda poetry. Whatever it is that will make you feel extraordinary, do it. It’s just one day out of the year that you absolutely deserve to be dazzled, just like everyone else.

Valentine’s Day Dos:

• Ask someone out for a rendezvous on Valentine’s Day (even if it’s a first date) and make them feel as special as you would on any other date.
• Add a little bit of flair with a single rose, a selection of chocolate, or any other type of simple acknowledgement that here you are, together, on a day that’s designed to make people feel exotically special.

Valentine’s Day Don’ts:

• Sit at home alone and sulk.
• Send messages out of desperation to an enormous amount of people online because you are eager to experience any type of in-person connection on this holiday.
• Consume too much wine, chocolate, or episodes of Sex and the City (alone).
• Turn down a potential suitor just because you find it “pressuring” to go out with them on Valentine’s Day.

Want to be my Valentine? Contact me here: www.thethingsilearnedfrom.com

There used to be a time when we were all not so scared of using the telephone.

Do you remember the days when you used to have your best friend’s phone number memorized? Or how you’d beam with excitement and your tummy would swarm with nervous butterflies when your mom would shout from the downstairs corridor, “Jennifer, there’s someone on the telephone for you.”

Today, I have friends that don’t even know their significant other’s phone number by heart. While they do know their Twitter handle or their Instagram name, that won’t help them one bit if they were to be stranded somewhere, face-to-face with a payphone. They’d only be able to communicate by typing a message in 140 characters, or less.

With the cold weather making us want to hide underneath a blanket (note: if you live in Florida, or somewhere else tropical, that blanket has holes and those holes are nicely filled in with sunshine—so enjoy!), it’s often difficult to muster up the amount of clothing and energy required to leave the heat that radiates from between our couch cushions to attend a first date. And if we do make that first move, we often spend the first couple of “getting to know you” minutes defrosting, or like me on my most recent first date, dealing with an unattractive case of a nonstop running nose.

How about breaking the ice (until summer time can do that for us) with a preliminary get-to-know-you phone call-date before meeting in person?

Do: Phone your new friend during appropriate hours. No one appreciates an energetic “HELLO, I’m Jen!” as their early morning wake-up call at the dreadful hour of 8am, or as a late night booty call at the lazy-eyed hour of 11pm. If you’re going to make the move of dancing your fingers on the keypad, do it at a respectable hour.

Don’t: Stray away from rehearsed “about me” speeches, or a set of designated job-like interview questions. On the phone, you should give off an inherently relaxed tone, as if you were having a conversation with someone in person. Carry a casual and flowing conversation, taking a deep breath during natural pauses and creating an infrastructure that will be easy to build on top of once you meet up in person.

Read more of Jen Glantz here: www.thethingsilearnedfrom.com

Back in the day, when it was more standard to receive letters in the mail, I used to go bonkers at the site of an envelope addressed to me, decorated with carefully placed postage and saliva-sealed edges. Through the years, that excitement carried on through the finger-print stained notes I’d get passed during class, “You’ve got mail” notifications for new emails (minus, I will add, work emails), and now 100hookup messages.

The prospective “what-if” that dazzles my imagination when I see the flicker of having a new message lying idly in my 100hookup inbox is enough to make online dating become an obsession — or at least a mid-afternoon pick-me up!

But not all 100hookup messages are created equally. Some are laced with time consuming references that some charmer took from my profile in order to prove to me they took the time to “learn more about me” and to critique me, past my selection of selfie-posted pictures. And some, the ones I normally don’t reply to and instantly press delete on, are practically blank messages, one worded, or the absolute worst, contain a scrambled together use of punctuation resulting in a ; ) symbol.

Do: When you’ve landed on someone’s profile who makes you sneak a smile, and while dabbling through their “details” your heart flutters, and your mind travels to frank possibilities of a future with them, or more simply put, a first date—send them a message! Send them a message that has personality, one that uses a variety of punctuation, admiration, and thought. Tell them about something on their page that made you pause and become momentarily intrigued. (This “Do” is also for all my single ladies. It’s acceptable and impressive for you to send a guy that makes your heart wiggle a message. Don’t play hard to get, play go out and get them.)

Don’t: Don’t start and end a message with only three letters: “Hey.” If you’re going to take a humorous or cliché route, like a recent message I received that said the following, “Judging your book by its cover, I’d love to curl up and read the rest,” include more context and more details that begin a fluid conversation (including your name). I would like to be able to respond and not be utterly creeped out.

When I first told a small group of my closest friends that I was going to join 100hookup, one of them (who has spent a couple of months on the site), turned to me with endearing and enthusiastic eyes and asked, “What’s your plan?”

Plan? What kind of plan did I need? Don’t I just set up a profile with my “who, what, where, why, and when,” and just wait? Did I need to make a to-do list, or a color-coded chart to handle my new wired up dating life?

I told my friend that my plan would include simply emailing any guys I had interest in to set up a date. “Email?!” she said with a non-stop laugh. “That wont go over well.”

Before I joined the site, I was wary about giving out my number. I have a very close-knit relationship with my phone, it goes everywhere with me, even the bath tub (thank you overprotective phone case). The last thing I want is a swarm of text messages from a jumbled mess of men I wouldn’t be able to place a face to a name to… yet. My “plan” of action would be to give out my phone number to a guy, but only after we met in person, and only if we really hit off.

After spending a week on the site, and having several requests to exchange numbers, I quickly realized the only sense of a “plan” I had going into this was suddenly an ultimate failure. I was even turning off guys where I thought there might have been potential. When someone intriguing asked for my digits, I’d say something awkward and nonsensical, making me seem mistakenly distant or uninterested.

So, here’s what I’ve uncovered about sharing your digits:

Don’t: If you’re still not sure you like someone you’re chatting with, and feel as though you need to go on bantering a little more online before handing over your digits. Keep the conversation flowing and casually mention you’d like to keep getting to know more about them before meeting up. If they are turned off, or make you feel uncomfortable, accept this as a possible red flag.

Do: Give out your digits if you feel like you’ve hit it off with someone and wouldn’t mind a quicker chat to occur via the dancing of thumbs on your cellular phone. Also, do give them 500 bonus points if they take your digits, and instead of admiring them, they actually pick up the phone and call you to ask you out on a date.

It’s been almost one year since I stuffed my entire life into two 50-pound suitcases, smooched goodbye a life underneath the Florida heat waves and moved to New York City. And throughout my adventure here, having to navigate my way around cohorts of tourists and consciously avoiding getting swiped by speeding yellow taxi cabs, the two most popular and regular questions my loved ones back home dare to ask me are: “Are you surviving the weather?” and “Did you get married yet?”

My constant response to both always comes decorated with a deep-pitted sigh and a fumbled laugh: “NO!”

Let me rewind for a second. I moved to New York for the same reason most 20-somethings drain their savings accounts: to live inside a shoe box, eat the crust of days old bread here, and to flirt with adventure. I came here to jump start my career and be spoon feed a constant reminder that every moment I spend swallowed between my couch cushions would set me back an indefinite amount toward reaching my wildest dreams. However, with quite a large number of people cha-cha sliding around such a small city, if I did, by chance, meet a guy who would look at me with the same kind of goo-goo eyes that I only save for a delicious slice of street pizza, well then that would be a great added bonus, and a exhale of relief for my mother.

I always thought I’d meet someone naturally. Perhaps while reading through 100 pages of a Norah Ephron novel in a bookstore, or while tapping my toes in line to get a fresh, hot bagel with some strawberry shmear. I’ve spent my Friday nights in a cesspool-like environment, covered up as a West Village bar, making small talk with guys that reek of Whiskey and then lost track of my Subway stop because I was gazing into the eyes of a cute straphanger. But nothing. There’s been no connection worth writing home about — and most of my first dates end with me wallowing on a warm bench alone, declaring my love to a pint of Chunky Monkey.

It’s been almost a year. Now that I’m finally settled into working at my 9-whenever-the-day-ends-job, and can finally traverse the city (or at least the parts of the cities with numbered streets), without whipping out Google maps, it’s time to focus on navigating my heart.

And in the process, I fancy to share all the gory and beautiful details with you, my new 100hookup friends, about the dos and don’ts of first dates (the awkward hellos and the even more awkward goodbyes).

All to finally be able to bring a mensch home to my darling parents, all in the name of hoping to find “Love at First 100hookup”.