Michelle was in her mid-20’s and was tired of being pestered by her Mom, Janice, to find a nice, hookup husband. So much so, in fact, that she told her mother that she was absolutely forbidden from setting her up on dates. Michelle needed boundaries with her hookup mother (don’t we all?) and she was adamant about finding her Beshert on her own. So, when Janice was approached by her good friend Karin who wanted to set up her nephew with Michelle, Janice politely refused because she wanted to respect Michelle’s wishes. But those same boundaries didn’t automatically apply to Karin and so she called Michelle directly. Of course, Michelle called to yell at her mom, but Janice was just as surprised as Michelle was that Karin took it upon herself to call! Michelle went ahead and met Karin’s nephew… and 30 years later they’ve been married 28 years with 3 kids and 1 grandchild.

Michelle didn’t want her Mom to set her up, but at least she was still willing to allow someone else to play matchmaker! Are you accepting every date you’re asked out on?

Recently, I went on a very formal first date. I was flabbergasted when he showed up with a giant bouquet of flowers. I’m rarely speechless, but I think the flowers overwhelmed me from the start. While I appreciated them, I had no idea how to interpret the gesture, and was a bit freaked out. They’re still brightening up my apartment though, and now I can breathe easier knowing that they aren’t a declaration of love by someone who I’ve known for less than two months.

We went to a symphony and dinner, ate dessert, and sipped wine. I felt a bit out of my element; I’m more accustomed to starting out with a low-key first date. Being wined and dined isn’t something I expect on a first date. I just like to talk, laugh, and get to know each other in a casual setting. I decided, after a lot of confusion and conflicted feelings, to give this guy a second shot to wow me… in a way I am used to and comfortable with. So we went to a casual dinner, walked around a park, and had ice cream.

After the formal date:

1. I wasn’t sure if I wanted to go back out with him and felt bad about myself
2. I was exhausted trying to interpret what had happened on our date
3. I didn’t think he was able to read my signals and vice versa

After a candid discussion and a good dose of humor, he asked if he could try again in my style. No red carpets, no flowers.

 After the casual date:

1. I felt at ease and able to talk more freely
2. I thought we had much more in common and walked away feeling good about myself
3. I had no problem sending or receiving his signals

When planning a date, make sure to think about who you’re dealing with. Not everyone likes the same kind of first date. Starting out with daytime coffee is a great go-to if you’ve never met. If it goes well, you can extend the date. If not, you only waste 45 minutes to two hours of your life. It’s not super creative, but it’s tried and true. If you have met before, try to match the date to their preferences. Some people might love skydiving as a first date, while others might have a panic attack. I am in the latter camp. I would avoid trying to sweep someone off their feet on a first date. There’s plenty of time for that later on in the relationship, and you may end up accidentally sweeping them out of your life.

Often times when I go on first dates, I’m asking myself (prematurely) if I can see myself having a future with this person. But not just a future in the sense of multiple dates… but in the sense of marrying them and spending the next 60 years with them. And did I mention this is all happening after chatting for just one or two hours? All that pressure sometimes ruins my initial perception of a person and instead of having a good time on a date, I find myself having these internal battles with myself.

Here’s what you should do instead:

• Do: Dates 1-3 should be measured based on how well you get along with a person and, of course, how much fun you have with them. Do they interest you? Do you want to see them again next week? Make your judgments based off those questions.

• Don’t: Start picturing your wedding or your old-age days with this person. They will see this internal battle on your face, in your gestures, and in your responses. It’ll make you seem and feel disinterested in someone who could potentially be a great match.

Follow Jen here: @tthingsilearned

When I first joined 100hookup, I went out for tea with a guy who had me running home and telling the world that I had found “The One.” The over-dramatic monologue I was preaching to my friends was cut very very short, when I never heard from him again after our first date. Almost seven months later, I checked my 100hookup inbox and received a message from him. What’s a girl to do? Go backwards and give someone a second chance after not hearing from them in months? Or keep moving forward and ignore their attempt at seeing you again?

• Do: Listen to what they have to say. Hopefully their message to you “explains” where they’ve been and why they didn’t contact you after the first date until now. Read their message and decide from there if you want to give this person a second chance.

• Don’t: Distract yourself with someone who isn’t right for you by pretending they are. If they are messaging you like they have no idea who you are — and clearly have forgotten ever going out with you the first time — ignore them. They are not worth your time and will easily forget you the second time around!

Read more from Jen at www.thethingsilearnedfrom.com

Last week, I wrote about deciphering the right time to get into a Facebook “friendship” relationship with someone you’ve just started dating. And while that’s bound to happen at some point in your courting, it’s also important not to judge someone based on what you find scattered throughout their social media trail. The other day, I was spitting out lines on the phone to my mom about how I didn’t want to go on a first date with a guy because I didn’t think we were a good match. My only justification for this claim was solely based on what I knew about him from social media. Was that a good enough reason to write someone off and skip out on a first date?

• Do: Practice self-control if you have access to someone’s social media accounts before you’ve met them — and refrain from doing a thorough investigation on them. If you can’t control yourself (which, power to you if you actually can), try to digest the information by reminding yourself this is just a small representation of who they are. Think about what someone might think of you if they read through your 1,000+ tweets before meeting you. It’s worth giving someone an in-person chance.

• Don’t: Cancel a date because you’ve seen too much on someone’s social media accounts. If you’ve stalked them to the point that you’ve seen photos of their ex-girlfriend or you know what they looked like at their Bar Mitzvah, that’s your fault. Ignore the fact that you just freaked yourself out and go meet them in person. Then, you’ll have the information you need to judge if you’d like to continue seeing them in real life… or just through the internet waves.

Read more of Jen Glantz: www.thethingsilearnedfrom.com
or follow her on Twitter: @tthingsilearned

There are people who “try” online dating for a month or two, and then call it quits. They will go back and forth through a series of messages, venturing out from behind the computer screen for a date or two (which inevitably won’t go exactly as planned), and then decide enough is enough. They then throw in the towel and resort to living a lonely life of sinking into the creases of their living room couch, playing unlimited games of Xbox, and ignoring calls from Mom — because all she will nag about is why her kid is wasting their lives holding hands with a remote control. Here’s when you should give up… and when you should keep on, keeping on:

• Do: Give the online dating scene a chance. If it doesn’t work out, maybe take a short break, and come back to it refreshed and open to trying it out again. Sometimes it helps to just revamp your profile, or spend some time rethinking what it is you are looking for in a person and how serious you want to take this experience.

• Don’t: Go on one or two online dates and call it quits. Most first dates will be a little overwhelming or awkward, but that’s why there is sometimes such a stigma around first dates. Either decide to go on a second date with someone who has potential, or keep searching and corresponding with more people until you find someone else who sparks an interest in your head.

There is someone out there for everyone — the number of different types of online dating sites just reinforces that! Give it a chance, or two.

Read more of Jen Glantz here.

Just the other day, while on my way to meet a strapping gentleman for our first date at a restaurant in Chelsea, I found myself flustered and in a bizarrely terrible mood. I was running over 15 minutes late, stuck on a conference call for work, and though I had enough time to take a shower I didn’t have enough time to dry my hair, forcing me to exit my apartment with a wet mop of tangled split ends resting awkwardly on my head. When I finally stumbled my way into the arms of my date for a friendly “hello”, I was still huffing and puffing and feeling like a 5”7 catastrophe.

I noticed that when I started unloading my hectic day on the salad plate of my date, he began looking soggy, uninterested, and unsure of what to say or to do to cheer me up. I realized this complainer was not who I was! I quickly apologized and vowed to never again unleash these kinds of dragons during first impressions. Instead, I decided that next time I’m faced with chaos before a date, here is how I will deal with it:

Do: If you had a tricky day, call a good friend before you head out on your date and spend a few minutes venting to them. You should always try to put your best peep-toe forward when marching into a date, so a good a venting session will help clear your mind and bring you back down to earth.

Don’t: Leave your problems at the door. If you had a terrible day at work, just got into a screaming match with your darling parents or are finding yourself overwhelmingly tired, check these things with your coat and don’t bring them with your handshake when you go to meet your date. It’s okay to allude to them briefly, in a joking matter, mentioning the tough day you may have had, but why harp on it? The point of a first date is to get to know someone, so show off the things that make you energized, happy, inspired and motivated on a daily basis.

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

I have gone broke from a first date more than once. Somehow, going on a date just extracts the paper bills from the inside of my pleather wallet without me realizing what’s happening. Once, a few months ago, going on a date even forced me to overdraw my bank account. Talking about who should pay for a first date should be on the list of topics for the next presidential debate (just kidding), as it warrants much emotion, opinions and even deal-breaking decisions by those who have rules and guidelines tattooed in their minds.

Here’s my breakdown on the payment plan for a first date—this one is targeted to the girls:

• Do: Always offer to contribute on the first date. You both mutually decided to go out and “meet” each other on this awkward rendezvous and it’s only right you offer to shell out the cash for your half of the meal, or your gulp of a full glass of Pinot. You can follow your own rules on dates two through infinity. However, you should use your manners and offer to pay on the first round.

• Don’t: Turn your shoulder on a first date who makes you pay. Yes, it’s lovely to be wined and dined on occasion, but it’s best to consider a first date with someone as a friendly meeting. A “let’s get to know each other—on a surface level and go from there” kind of thing. Don’t be upset or feel as though you’ve been stiffed.

Read more of Jen Glantz here.

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”.

1. Not all Jews are created equal. As a Reform girl, I learned quickly that dating someone much more religious than myself was not right. I also learned that Orthodox Jews’ iPhones are not immune to Shabbat. And I promise you I was bat mitzvahed.
2. Sometimes your date can go so badly that halfway through your first drink he will say, “Yeah, this isn’t going well.” At this point, feel free to ask them if they have friends to set you up with. Obviously, this isn’t always protocol but if it’s that apparent you’re both having a bad time, why the hell not?
3. Not everyone wants a serious relationship. Some 100hookuprs want activity partners, not someone to bring home to the fam. Try and get to the bottom of this before you hit date #5 and wonder why that ohmygod-this-is-amazing spark is going out faster than you can say afikomen.
4. Sometimes you might flee a date (see: Stage Five Clinging Salsa Dancer) and then see that person while you’re on another first 100hookup. And it only takes 15 minutes of them giving you the stink eye for you to realize it. I like to call this 100hookup Karma.
5. Not everyone tells the truth about their height, their weight, their looks. But everyone wants a chance in real life. And if you’re not willing to be open-minded, don’t say yes to the date. It’s not like when you say yes to a first date that you are automatically signing on for a second or third one. So if you’re even a tiny bit curious, give up an hour of your life to see for yourself.

Okay, I lied there is a 6th lesson…

6. Sometimes a date can go well. It can go so well, in fact, that you leave the date and feel so unexpectedly excited that you grab your phone to call your friends and tell them everything. And you stare at your phone waiting for them to call or text you. And your mind wanders down that road where you see future dates play out. And then everything that happened in lessons 1-5 slips away and you’re in the moment and it’s a good one. And it was all worth it.