HOW TO MAKE YOUR FIRST DATE WAY LESS AWKWARD

First dates can be a real freaking bummer. You get dressed up, you do your hair, you shower. You hope and pray this isn’t awkward af while you’re in the Uber and when you arrive you have to pretend to be interested in everything your date is saying even if that means stifling a yawn when he goes through the entire beer menu and tells you if he’s tried each one before.

I get it. It can be totally nerve-wracking and why wouldn’t it be? You’re meeting a stranger essentially with the possibility of romance lingering in the air. It can easily feel forced and weird if you let it.

As an expert first dater (my new job title) I’ve compiled my top 9 tips for making your first date more enjoyable and less painful! Good luck!

#1: WEAR SOMETHING COMFORTABLE

I have a few pretty standard go-to date outfits that I wear because they make me feel the most like myself. I don’t wear anything tight or low cut because I don’t want to feel self-conscious about him staring at my boobs all night (note: this will happen regardless). If you’re into that, by all means, do what you gotta do. But choose something you’re genuinely comfortable in, not something you think he’ll like.

You obviously want to look nice so sweatpants are out of the question unless you’re going on a date to the gym in which case I’d like to ask you to exit out of my blog because you are not my people. Just kidding. Kind of. Sorry.

Wear a blouse you love that you always feel confident in. If you love dresses, wear one. Just pick something more on the casual side. Don’t scare him away with your ball gown and tiara. You want to look like you put some effort in without making him wonder if you’re attending the ballet later that night.

There is nothing worse than already feeling nervous and then having to readjust your jeans every two seconds because they’re too tight or constantly having to pull up your strapless bra. Wear something comfy that you know is flattering and move on. You want to feel your best and not be distracted wondering if your stilettos are going to puncture your heel at any moment.

I personally usually wear high waisted skinny jeans (aka eating pants), a lace trimmed cami or cute cropped knit sweater, booties and a moto jacket. I feel cool and pulled together and casual without looking like a slob.

Stay tuned for a post dedicated to date outfits!

#2: MENTALLY PREPARE…WITH ALCOHOL

If you don’t drink then this may not apply to you but if you do then read on!

Listen, this shit can be seriously anxiety-inducing. Even as someone who has in all honestly probably been on over 100 first dates (I feel like that might even be a little low) I still get a little nervous.

I learned long ago that being the best version of myself meant being comfortable and confident. They don’t call it liquid courage for nothing!

I like to have a healthy glass (aka two) of wine before I leave for my dates. Obviously, I take Uber and I don’t drink in excess when I get there. Most of the time.

The wine mellows me out so when I show up the conversation feels less forced and I’m generally in a better mood. I don’t show up drunk. Just happier.

I’ve taken a shot before too and that also does the trick but I highly recommend limiting yourself to just one pre-game drink (unless it’s wine, which has antioxidants so you’re essentially adding years onto your life) so you don’t waltz in slurring your words and asking if someone can put on Beyonce.

You might not be nervous or feel the need to calm down BUT some of us are here for a good time, not a long time so don’t judge me!

Plus as a bonus, if your date sucks you won’t be as pissed.

#3 THE AGE OLD DINNER VS. DRINKS DEBATE

I can’t remember the last time I’ve gone on a coffee date and honestly am more of a fan of evening dates that take place in low lighting so I can slip out into the night if need be.

You might find yourself feeling inclined to suggest dinner when in the planning stage and while that’s fine, if you can help it, I would go for drinks.

I’ve been on great dinner dates and that’s nice and all but a lot of the time you end up stuck with this guy for hours through an entire meal. It feels formal and forced. You can’t relax and bask in the comfort of knowing you can leave at any point if you’re bored or creeped out.

Dinner is nice. There is nothing wrong with a guy asking you to dinner. It’s the standard date format, but in my opinion, it’s a little tired. Try suggesting something creative!

Here in San Francisco, we have a ton of fun activities you can do that are accompanied by alcohol, making the evening ten times more enjoyable in my opinion (I realize I am beginning to sound like an alcoholic but hey, I am who I am).

I’ve gone on dates to Urban Putt, an indoor mini golf bar in the Mission, that were a blast. You could go bowling at Lucky Strike or play old school arcade games at Brewcade. If you’re not a San Francisco local do some research to find cool activities in your city.

And if you want to go old school on this one I am always a fan of the “let’s meet for drinks” style date because it leaves things open-ended. If you like each other you can hit up another bar. You can even get food after. If there isn’t a spark you can ditch him after one drink and walk down the street to get pupusas. It’s a win-win!

#4: PICK THE PLACE IF YOU CAN

If you’re super adventurous you may be down to just go with a flow and try a new spot he suggests. That’s totally fine and I do this often because I love finding new places in San Francisco.

However, if you’re new to the dating game (especially the online dating game) and you’re already feeling anxious af, meeting in a familiar environment might calm your nerves.

Depending on the type of guy I’m meeting and his interests I have a ton of places I usually recommend if they ask my opinion. There is one bar in the Mission that I recommend the most for several reasons.

Casanova (16th & Valencia) is this dive bar with super low lighting and strong drinks. They have comfy couches and tons of seating and most notably, a ton of erotic art on the walls. It certainly makes for a good ice breaker! It’s funny, it’s cool and I’ve been going there for years so I always feel at home.

Another reason why I love taking dates there is because it’s in a neighborhood I love and am super familiar with. I can easily recommend other bars or food spots off the top of my head if the date continues. We don’t have to walk aimlessly or google it. I get to be the best tour guide ever.

Finally, I love Casanova because it’s only a ten-minute drive from my house. I can make a quick escape if I’m not feeling it!

If you can pick the place, suggest somewhere you like and know so you can feel comfortable and at ease instead of awkwardly searching for the bathroom and taking 10 minutes to look at the cocktail menu.

#5: GETTING THERE FIRST IS LAME AF

Okay, this seems rude so bear with me on this one.

I am not telling you to be purposely late. I am just telling you to be fashionably late.

I’m talking a five-minute window here. Don’t be an asshole and show up 20 minutes late because your “lyft driver doesn’t know his way around the city” (aka my excuse always. Immediately regret publishing this and revealing my secret). But showing up for an 8 o’clock date at 8:03 is fine. And hopefully, he’s not the late asshole and will be waiting for you patiently outside.

There’s just nothing that psyches you out more than waiting outside in the cold, hands gripped tightly to your phone, checking his tinder profile, again and again, making awkward eye contact with any man who walks by.

Of course, you can’t always guarantee that you won’t get there first so if you do and you’re feeling uneasy, my advice to you is to go inside. Yes, you read that correctly. Do not wait for him outside unless you’re meeting at a restaurant. If you’re meeting for casual drinks then go in and grab a seat. Order a drink. Take a load off. Text him and ask him what he wants. Be that girl. Don’t shiver in the cold and pretend to be texting. Come on.

You’ll seem cool and comfortable with yourself. Which is ultimately, the goal here.

#6: KEEP YOUR PHONE IN YOUR BAG

There is nothing that I think is ruder on a first date than someone who checks their phone. I’m getting heated just thinking about it. I’m a blogger. I’m on my phone 24/7. If I can keep my phone in my purse for 2 hours then so can you.

If a guy has his phone on the table, is constantly glancing down at his “pocket” or just flat out has the sound on and checks any text that comes through, I’m over it. He’s clearly uninterested in getting to know me and will probably die alone or have to build a female robot because no one is putting up with that shit.

The same goes for you. It doesn’t matter if you promised your friends you’d give them an update (isn’t that what bathroom breaks are for?) or if you’re waiting on an important work email. You’re sending the message that you don’t value the other person’s time and that your little rectangular screen is far more interesting than they are. #rude

I only take my phone out when my date uses the bathroom (and I promptly place it back in my bag when he returns) or if I’m showing him a picture. Otherwise, zero texting, Instagramming or snapping. Even if I don’t like him or the date isn’t going well. You both agreed to spend this block of time together so you should honor that commitment. Unless he’s a murderer or loves Nickelback.

#7: FILL YOUR FRIENDS IN

I know I just ranted about not texting your friends during your date but you should still keep them in the loop.

When it comes to my friends I am not a very private person (I’m sure some of them wish I were! Ha!) and I tell them basically everything. Especially when it comes to guys. Most of them are in relationships and I think like living vicariously through me. Or more likely love hearing my terrible date stories so they can fully appreciate their significant others. Whatever.

Anytime I go on a date I tell my friends beforehand and send them his picture and we make fun of his profile and I show them outfit options even though I always wear the same thing. It’s a ritual.

They always know the date and location so they can check in and they’re always available to call and pretend to be my mother with a life-threatening emergency (sorry mom) if need be.

We’re also creepy friends and track each other so I’ll let me friends know I have a date so they can hopefully track me and potentially avenge my death if things don’t go as planned. Again, kidding! Kind of.

It just feels better knowing that from a safety standpoint, people know where I’m at, and also from a moral support perspective, I have my girls at my fingertips (ew, regretting that choice of words).

#8: DON’T BE NERVOUS, SERIOUSLY

I know dating is hard and can feel super life and death at moments (it’s definitely not) but I promise you, you don’t have to be so nervous.

The worst case scenario is that you’ll have an awkward first date story to make your friends laugh. You only have one life to live and dating is so not the end all be all. Go on your dates and feel excited. Think of them as just a fun outing with a new friend. Because that’s all it really is. If the date doesn’t go well, the date doesn’t go well. You’ll move on and you will survive.

The fact is, you’re not going to fall in love with every guy you go on a date with. You’re probably not even going to mildly tolerate most of them. Why do you think I go on so many dates? You have to kiss a lot of frogs. Or just endure their tragic lack of social skills for an hour.

You might as well just enjoy each date for what it is and not go in with grand expectations. I’ve been on dates where they went so well on my end but the guy just wasn’t feeling me. I’ve also been on a lot of dates where I felt like we had zero chemistry and he couldn’t stop calling me for weeks after. Only time can tell you how things will play out with the other person so instead of putting so much pressure on yourself and this date just treat it like it’s no big deal. I don’t mean show up looking like a hot mess and farting or something. I mean, treat it like a casual drink with someone new that may or may not lead to something.

I promise shifting your mindset will take the pressure off and relieve some of your nerves.

#9: NO EXES, NO TANTRUMS, AND NO COMPLAINING

If you’re having the worst day of your life, maybe don’t go instead of showing up acting like the Grinch.

Obviously, you want to be your true, authentic self, but you still want to be the best version of your authentic self. This means that some topics are just simply off limits.

Even if he brings up an ex, do not indulge him. Change the subject and move on. Do not take that as an invitation to show him the last text your ex sent you and to rant about that time he forgot to call you back for 6 days in a row. And definitely, don’t bring the subject up on your own! Eek! It makes my skin crawl just thinking about it!

You’re on a fucking date, now is not the time to bitch about your ex and how he ruined your life. Your date will not find this attractive. He will not think “Oh wow, she has so much baggage, I would love to mend her broken heart”. He will think you’re crazy and resentful and CLEARLY not over your ex. Save those conversations for your best friends who are stuck with you have to listen to that annoying bullshit. Don’t torture this poor guy!

On a lot of dates I’ve been on the guy will ask me if go on tinder dates often (the answer is always “I’ve been on a few” #smooth) or when my last relationship was. I simply answer and move on. If he gets really curious and wants to know why we broke up I do not then share the sob story of being dumped on the side of the road on our way to get soup dumplings. No. I say “We dated for a year and realized we just weren’t right for each other” and MOVE ON. I suggest you do the same!

So the tantrums thing is probably super obvious and maybe I didn’t choose the right word. I am not under the impression that any woman in her right mind would fling herself onto a dirty bar floor while hysterically screaming because she wanted a vodka tonic, not a vodka soda. I’m talking about those mini, high maintenance meltdowns that you should really talk to your therapist about.

If a waiter is taking a long time to take your order, if you can’t get the bartender’s attention or if a girl walking by accidentally bumps into you and spills your drink all over you, keep calm. Don’t be that entitled, rude brat who cops an attitude when things aren’t going her way. Don’t complain. Don’t sass the server. Don’t raise your voice. Behave. Be the girl who goes with a flow and has a good sense of humor about less than ideal circumstances.

I find guys who treat people in the service industry poorly immensely unattractive and it’s a total deal breaker for me. The same goes for a lot of guys so think before you speak.

Finally, no one likes a complainer. There’s nothing wrong with sharing a funny anecdote about a time when things didn’t go your way or mentioning that you’ve had a “hectic week at work” in passing. But remember, this is a first date. This person does not know you and if you spend the majority of the evening complaining about your boss or your parking ticket that’s the impression he’s going to leave with. Be human but save the complaints for date 6.

If you’re getting ready for a first date soon I’m sending you endless good vibes and I hope you have a fabulous time!

Share your awesome (and not so awesome) first date stories in the comments!

Xoxo,

She