The Best Way To Go From Day Drinking To Fine Dining In San Diego Solo!

Last Thursday I had a really incredible day date out on the town of San Diego. My day date was with myself. (Date yourself! more on that at the end of the post) Which then turned into a full on night out which was unexpectedly awesome. You can never chase the dragon when your going out for entertainment. The dragon must come to you. If it's not there then do yourself a huge favor and go home. That is why the best times come when you go with the flow of the day/night rather than against it. Today I'm going to walk you through how to go from day drinking to fine dining in San Diego in style on a Thursday because Friday's are overrated.


For me, a Canadian expat currently living in Tijuana it starts with a walk across the border. This is the San Ysidro Border Crossing that divides North and South America. This border is what all the fuss is about. Migrants, drug trafficking, human trafficking, illegal arms.. and of course hundreds of thousands of Latinos crossing the border to work in the USA every day. The Pedestrian line this day had me standing outside in the sun for 25 minutes. Considering how many people there where to process ahead of me all in all reality that's actually fairly quick.



Now let's zoom in on the culture for a moment here in Tijuana shall we.. Can you see the breast mug in the middle of the religious statues?  This photo is the antithesis of Tijuana and what it represents. A a rock hard implant in your face at a strip club while praying to god.


On with the show.. My first stop after crossing the border into San Diego was Tabac Cafe & Hookah Lounge. Always start day drinking with food and a non-alcoholic beverage. This is so key so you don't get too boozy before sunset. 


It was a good pick for a quick bite in a relaxed environment. I don't smoke but for some reason I really don't mind the smell of Hookah around me. The ambiance was quaint. It's dog friendly. The chicken salad was surprisingly really good here. However, they where playing Usher & Rhianna which was the only thing I would have changed. It did not suit the vibe of a middle eastern themed lounge at all. It's not a very social crowd that goes here in the day. It's great if you want a quick bite without interruption then to move onto your next more social environment.


From here you can easily walk to our next stop. My all time favorite! Which is Fifth & Rose at Pendry Hotel in Downtown San Diego. Whenever I'm in San Diego I always make a stop by here. It's one of my top hotel bars that I've been to. Period. The Pendry hotel itself is also pretty great. I spent one night here back in May. The staff is always really friendly and welcoming. You definitely want to sit at the bar here if your solo so you can chop it up with the bartenders in between them mixing drinks. Fifth & Rose is also a much more social environment. For an upscale joint it doesn't feel stuck up or hard to fit in here. It's also absolutely gorgeous!

550 J Street

                 Ask for Nick the manager & tell him Tiffini sent you. They will take care of you.


While I was at Fifth & Rose I met some nice people. I got lost in a few great conversations and as the day started to turn to dusk I made a reservation at a speakeasy. People I meet are always telling me about this place when I'm downtown. They require you to text them first before you are given a time to be there which I did a few hours before I planned to arrive.



I was greeted by a very friendly front of house staff. May the hostess was awesome enough to take this video of me first entering the bar area. The entrance as you can see is a take on how The Houston Brothers in LA have set up their speakeasy style bars. They really revitalized that trend on the west coast and now I see how influential their work has been no longer living in LA and seeing their impact even in San Diego.

777 G St
I really loved the decor inside which was too dark to be able to capture on camera with their no flash policy (which is a great policy in this modern age). My blue day dress turned into this really groovy rust shade inside this bar which made me feel like I went though a wardrobe change for the night. I had the Dirty Program Martini. They had no wine options here for me to stay in theme booze wise with my day drinking. However, this was definitely one of the best Dirty Martini's I've had. Their garnishes are all pickled to perfection and there was a bit of spice to it as well. A must taste for all the Martini snobs out there. I am one! 

This is a place you go to just drink. Not to socialize. You come here for the awesome staff and super friendly bartenders who all make you feel taken care of. I stayed for one and then kept it moving. Glad I went, will be back but next time I'll go with someone so I don't feel so isolated. It's definitely not a social environment if your looking to meet new people. Patrons keep to themselves here.

Now let's get to the fine dining portion of our day out turned night. Any day of drinking is not complete without an impeccable meal at the end. I could not have went to a better place to cap things off at thanks to some sage advice from the staff at The Noble Experiment.


1909 India St
I have not enough words to fully describe my experience here. This is just that. An experience. I had the meatball and I swear to you I could still taste it in my memory the day after. It was incredible! The staff, the design, the lighting, the bar, the seats, the bathrooms. This place checked off every box and more. It's High Regality at it's finest. Want to know what that means? Click here for that  previous post.  


Born and Raised is also highly social! So you can go here solo as I did, have a seat on the bar side and still meet people. As I did. Not to mention there's a huge lounge area upstairs after you have your meal in the restaurant that has a ton of energy to it. I met a lot of people here that night. It was the perfect way to end the day. As I write this I already want to go back.

In closing before we get to my look in detail I need to remind you of how important it is to date your god damn self! I've been single my entire life. Sure, I've had relationships but nothing really long term or all that serious. As I get older each year I'm getting more and more into finding out what's going on with myself. Life is teaching me that there is need to wait for anyone. There will always be you here for yourself. Take the time out of your work life to continue getting to know the type of person you are becoming. Taking yourself out on dates is honestly the most fulfilling and rewarding experience one can have in this life. It's a high form of Romanticism and self love at it's finest. Being able to treat yourself to some time away from your routine and enjoy a day/night out is what this life is all about.

 The other thing no one talks about is how many more people you meet when you go out by yourself. Your not dialed into anyone's program but your own. So your program can easily change based on whatever happens around you. When your not tied to anyone your open to everything happening.

Use your phone sparingly, be present in the moment, talk to the wait staff and be open to the new people all around you. This world waits for no one yet is open to everyone all day and night long.







Style Breakdown:

Dress Gabriela Saga Creations of Lily - (Retail $300) $5


Patent Leather Purse Plaza Coronado - $15

Shoes Andrew Gellar TJ Street Shop - (Retail $100) $5

Shades Agaci - $5

Total Look Cost: $35


About Me: My name is Tiffini Truth and I'm a Power Tool Performer!


 I love style and this blog is my way to share my personal style experience with you when I'm not performing my live show in the studio. I have a weekly Podcast "The Metal Mindset" which goes live every Wednesday at 12pm PST. "This Week In Metal" is my Metal Art Youtube series.

Subscribe to get my personal styling advice on My Patreon Page so you too can also get the look for less online!

See you next Monday for more Metal Mouth Style










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