Makeup pro & casual photographer for older woman

Before I cautiously enter the world of online dating, I need to upgrade my look a bit.  More than a bit.  I own two lipsticks, and I'm still doing my eye makeup the way I did in college.  How long ago was that?  I'll put it this way: the year after I graduated from college, Richard Nixon resigned from the presidency (one of the happiest days of my life).  After I learn some new ways to look my best, I'd like to have some casual photos taken. They can be done by someone who's skilled with their smart phone. I realize the demographics of BPN trend younger than I am now, but maybe someone's mother has done something similar.  I'm in Oakland, willing to travel within the East Bay or (for makeup tutoring) SF.  Or maybe I should just join a book club...

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When I turned 60 a few years back I had headshots at a photo day here:  The services came complete with makeup and some clothing options.  I brought my own scarfs which worked nicely.  I had my hair done the day before so that my hair was at its best.  The pricing was very reasonable.  

For makeup, I like Benefit on 4th street - drop by and make an appointment for a consult session. Benefit makeup is pretty user-friendly (like big fat eye sticks and bronzer you can't mess up) and it's a low-pressure shopping experience. You can have them teach you how to use a few products and update your look. I also like to get my eyebrows and eyelashes tinted there - it's an easy way to look like you have makeup on even when you don't. And as you may have discovered, your eyebrows have a way of disappearing as you get older. Giving them a gentle tint really brings the spark back to your face and makes your eyes pop! Good luck.

Good on ya for getting out there again. Your post is funny and smart and your personality shines through!  You're going to have a great time!  While I don't have a specific makeup or photographer resource, I wanted to share a couple ideas about the whole "look" thing, especially in the context of photos.  FYI I'm a 64 y/o with similar attitudes about makeup generally:  A great foundation for mature skin is IT Cosmetics (I use Medium Coverage CC+ Nude Glow). It has some truly magical light-reflecting properties that photographs skin incredibly well but are not heavy, so you'll feel natural in it. It's been a complete game changer . Try their Pillow Lips solid serum too if you want to add to your 2-lipstick collection. I get mine at Ulta. Consider going to a new hair stylist and/or updating your glasses frames if you wear them. I've found that getting my eyebrows threaded (just ask for them to be cleaned up) and then have them do a temporary tint adds youthfulness and (dare I say it?) polish.  You could also add one of the "beauty" apps to your phone (like Beauty Plus) for something that softens lines without making you into a Stepford wife. Though I would say I honestly have felt this unnecessary with the discovery of  the foundation :-)  The phone does matter so you might think about what kind of camera your phone has (iPhones, Pixels are good). You'll be using it for more than one photo so it might be worth the investment. Even if you have someone help you with taking photos for your profile, practice taking selfies in different light (different rooms, outdoors, different lighting/placement) and different angles to see what's most flattering for you. It's a weird skill to learn but once you do you'll find it's fun. Good luck, and have fun with this new chapter!

If you don’t find someone independently for makeup, you can book a free makeover at Sephora (as long as you then buy a certain amount of makeup at the end of the consult). I’ve found the makeup artists are really respectful of the look YOU want and can help you find the right products for your look and teach you how to use them as you get your makeover.

Your post made me laugh! I'm sure you'll get some responses, but just in case I wanted to share that Sephora stores do makeup lessons and/or just makeup, you can book an appointment! And that way you can buy the products right there if you like them. Good for you - I think it's great and wish you the very best luck finding someone special who appreciates your inner beauty as much as your outer beauty!

 I am an older woman too. I suggest you go the MAC shop on 4th street and get a tutorial on make up, how to apply, what to use etc.

See if you can make an appt in advance. 

for photos I recommend Kristen Loken ( 510) 601-0321

good luck!