First Dates are the best...I mean worst

So I had a thought the other day.  I had my first date/"boyfriend" when I was 10 years old. And since I didn't marry him (because, eew... insert Kentucky/West Virginia joke here) I have continued to date. That means that I have literally been on this merry-go-round of love for almost 23 years. TWENTY THREE YEARS! You would think that with 23 years of experience, I would eventually be good at this. But no, sadly, I'm still playing at the amateur level for all intents and purposes.

But here's what makes it fun. I did a recent tally, and I've been on something like 15 first dates in the past year, plus or minus. And first dates are hilarious. They're awkward, they're occasionally awesome, but usually just a lot of build up to very little return. And these facts are fairly universal. I LOVE talking about crazy first dates with friends. If you've met me, you know I'm a story teller. And I really believe any situation is worth being a part of, as long as I can tell a good story afterwards. When I was in my twenties, this belief lent itself to some crazy stories that 30 year old Dulciña would never entertain now. But luckily this reasonable, don't waste my time chick didn't emerge until my late 20's so we still have all the stories to tell, usually over a glass of red wine.

For this post, I've decided to gather some of the favorite stories I've gathered from my own life AND the lives of my other friends who are either still in the market, or have gladly left the single lifestyle behind. I make the disclaimer now that if it sounds like you, um sorry. Take it for a compliment. Apparently, while I might be mocking you, I still like you enough that you have access to my blogger thoughts.

So without further ado, here are more Do's and (mostly) Don'ts for first-ish dates (some creative license has been taken to include the occasional second date).

DO pay/offer to pay for the first date if you get any sense that the lady is a traditionalist. Do NOT pull out an envelope with cash, instead of a wallet and say "Wow" three times when the bill comes, especially if you order the lobster and your date orders the cheapest thing on the menu and water.

DO offer the lady a compliment if you think she deserves it. Do NOT tell the lady on the first date any of weird kinky things you want to do to her private parts, feet, underarms, hair or really anywhere else when you've been out for exactly 30 minutes.

DO try to sound smart if you are. Vocabulary is important to some girls. Do NOT throw out words like caligynephobia to try to impress your dates when what your really saying is "hey you're pretty and someone has accused me of being this word that sounds like a venereal disease but is really just a way of saying that I was actually more socially awkward in my distant past than I am now."

DO send the flirty text with emojis if that's your thing after the date. Do NOT send the dick pic. Ever, preferably, for some women. But generally, if she hasn't seen it in real life, it is NOT the time to send it over via text message. Also, if you're at work and you send us a pic from your home bathroom, we notice. We KNOW the picture was just sitting in your picture gallery ready to be sent at the "right" time. And if you are sending it from work, DUDE, where the hell do you work? Also, google auto saves all photos, so now your dick pic is a forever part of her internet life. She will not be thanking you for that. Except for 1 or 2 of you. She may thank you. You know who you are.


DO be single when you ask someone on a date. Why I have to say this, I don't know, but apparently, it's a thing. Do NOT talk about your CURRENT 2nd wife (3rd if you count commonwealth) while trying to convince a girl to become your mistress/side piece. Not only is it terrible form in general, but the girl will go home trying to figure out if she somehow presented herself as sidepiece friendly.

DO offer to pay for drinks. Do NOT offer gifts on first dates, especially money.Call me old school, but if money is being exchanged before last names, that feels awful close to prostitution or at least escort-adjacent.

DO look good on a first date. After all first impressions are important, and while women may not decide whether or not they want to get with you on a first date, they definitely determine whether or not they are willing to. Do NOT look prettier than the woman you're going out with. If you're going to a simple bar on Tuesday, leave the three piece suit with matching ascot at home. Even if your orange gators or cowboy boots are your favorite accessories, perhaps leaves those as a special surprise for date number three or four.

Do NOT neg your dates. I really don't care which MTV jack-behind said this was a good thing to do, real women with self esteem will never respond well. If you deliberately want to be an ass, stay home and leave real women alone. Netflix and wine will always make us happy. Dates telling us that we're as cute as their exes but maybe not as a successful yet, can go suck a big fat lemon and stop wasting our favorite post work hours.

DO talk about what you're currently looking for in your dating life. Do NOT tell ridiculous stories about your exes that make you look like a douche. This should be self explanatory, but people really are dumber than you think.

DO ask someone if they had a good time on your date. Feedback is important after all. Do NOT assume they had a good enough time that now she'll want to cook you meals and perform sexual favors at your house (dude, you're still a stranger) on the second date if you only invite her to do so.

DO be yourself. She wants to get to know you, not your date friendly representative. That being said Do NOT let your freak flag fly on the first date. If your dates ask you what you're into, and you say 50 shades of grey-esque stuff/licking dirty toes/unicorn porn etc., the average female will immediately exit stage right. We really wanted to hear about your fantasy football league and obsession with rafting.


DO own your sports obsessions in a reasonable way. If #Knicktape is your thing and the G-Men own your fall, that's fine. Do NOT cry over sports on the first date. Your parents are still alive. Get yourself together, man. (And I say that as a huge Duke bball fan. I also don't go on first dates during Duke games because I know better)

DO go for a first date hug, and occasional kiss, depending on the woman and the overall vibe. Do  NOT take off all of your clothes while she's not looking and say "surprise, guess who came to join the party!"

DO say that your were not feeling the date/the vibe/the chemistry or whatever. Do NOT say that she was the best thing since sliced bread and then duck phone calls and texts like you're in witness protection.

DO ask questions on a first date. Do NOT take notes. Seriously. Paper and pen should never be a part of a coffee date.

DO be sensitive and listen to your date, especially if you have just met. Do NOT feel like this is the time to grab her hand and read her the poem you wrote about raindrops, lust & pain, or the song you wrote about the juxtaposition of your relationship with your mama and the time you were kicked in the balls that one time in grade school.

DO be honest. Google is the truth serum of us all. Do NOT tell me you were born in the wilds of some weird third world country that doesn't speak English, but your name really is John Smith.

Unfortunately many of us have been on the wrong side of the "Do NOT" column on our first dates, and yet we continue to put ourselves out there. Why? Because sometimes you make us laugh. Sometimes you make us forget the doldrums of  our normal 9-5 and excite us. Sometimes you look at us and make the efforts of the short skirts and tight heels worth it. Sometimes you smell or sound so good that we're seduced into trying one more time. And sometimes you do all of  that and provide wine. And for all of that and much more, when you say "Hey, are you free on Saturday?" we'll continue to say "Sure, what do you have in mind?" And humankind will continue to grow and love and thrive as it always has. And as it is always meant to.