Why Date Vanilla?
Why Date Vanilla?

The love of your life probably has a boring dating profile. But I’d never tell you to settle for someone you don’t like.

I’m talking about giving steady, consistent, kind person a real chance—because that’s what lasting love is built on.

Flash and fireworks fade. Substance doesn’t.

Date Vanilla means choosing person who shows up, listens, follows through, and makes you feel safe. It means widening your filters, giving green-flag partners three to five dates before deciding, and working with apps instead of against them. It means building a profile that reflects the real you—not some performative version designed to impress strangers.

I teach midlife daters, especially those returning after divorce, how to date with clarity, confidence, and a repeatable strategy. No overwhelm. No burnout. Just a practical playbook for building authentic connections that lead to real relationships.

About Me

I was with my ex for 18 years before finally leaving my marriage at age 41. Smartphones didn’t exist when I was last single, much less dating apps. I assumed my friends would set me up with their divorced guy friends and I’d be swimming in blind dates.

That happened once.

I realized I had to face facts: I needed to date online to meet people. So I got on the apps and did what most of us do—I chased the shiny profiles. The tall, hot, “has-it-all” guys. And I wound up anxious, confused, and begging for crumbs.

Then I met the man with the bland profile.

No fireworks at first. Just a kind, consistent, responsive human who kept me curious. By date four, he relaxed, his humor landed, and the chemistry snapped into place. Eight years later, he’s anything but vanilla—but his profile was.

That experience changed everything. It taught me that the goal isn’t instant chemistry. It’s finding someone who makes you feel good, safe, and seen. Someone you actually want to spend time with—not just someone who looks good on paper.

About Me
Press/Media Bio

Alyssa Dineen is a dating coach, profile strategist, and author based in NYC. She founded Style My Profile to help midlife daters—especially those re-entering the dating world after divorce—feel confident and successful navigating modern dating apps.

With 20 years of styling expertise, an art director’s eye, and her own personal dating experience, Alyssa teaches a practical, repeatable framework called Date Vanilla. Her approach helps clients ages 45–70 build authentic profiles, work with app algorithms, identify green-flag partners, and create real, lasting relationships.

Alyssa’s book, The Art of Online Dating, shares personal stories and actionable strategies for building confidence in your dating life. She also hosts The Dating Lab Podcast, where she explores midlife dating challenges, red and green flags, and how to date smarter—not harder.

Her work has been featured in The New York Times, The Today Show, Goop, NBC, Bravo, and Oprah Daily.

Featured In
Success stories from real daters

When I was ready to start dating after separating from my husband I was somewhat terrified and completely clueless about the dating app world. Alyssa helped me set up all my profiles advising me on which photos to use and what to say in my bio. And she shared so much of her own experiences which was so helpful in navigating this new landscape. I am so happy I connected with her. She’s my dating guru!

-K.K.

It’s like Alyssa waved a magic wand over my dating profile. The quality of my matches went up exponentially!

-Tamara F.

I didn’t really have pictures that accurately reflected my personality. From the very first conversation with Alyssa, she instilled in me a confidence that she understood my challenges. The photo shoot was professional and comfortable and, frankly, a lot of fun. I’m seeing a much different (significantly improved!) mix of people in my “match” queue!

-Steve R

Before I came to Alyssa, I wasn’t getting the results I wanted from the dating app I was using. She immediately identified that I was on the wrong app and my photos were sub par—too many with other people, none where you could really see my face. And my bio wasn’t interesting enough. I made just these few changes and was shocked at how many more quality matches I got. Alyssa’s profile makeover and strategies were a complete game changer.

-Andrew B

I have truly enjoyed this process of setting up my online dating profile. Working with you and your team helped me find the image of myself I really want to present. I was at such a loss as how to get started. You have a great service!!!

-Janine Flasschoen

I wanted to let you know how much fun I had with you and your team [for my Profile in a Day]. You guys are a lot of fun and made me feel very special. You doing amazing job!

-Craig

If I hadn’t followed Alyssa’s advice, I wouldn’t be with my perfect partner right now. I thought I’d had a good profile, but she made a lot of changes and I started getting significantly better matches right away. (I guess my profile hadn’t been as good as I thought!) One of those matches turned into a very good first date, an amazing second date, but then the third date wasn’t as fun and interesting. I figured we ultimately weren’t the right match, but luckily I talked to Alyssa before I was going to end things. Alyssa heard me out, asked all the right questions, and coached me through why I should still go on a 4th date. And thank goodness she did. We’ve been together ever since and couldn’t be happier. So thankful I listened to Alyssa!

-Bryan H.

Thank you so much for making our Profile in a Day session so enjoyable, relaxing and comfortable. I felt like a king!

-John Healy

Thank you Alyssa! My Profile in a Day was just amazing. You are so talented— I felt comfortable and confident in you from the minute we spoke by phone and on the day of the shoot, all was pulled together. And wow, some of the photos shock me… so good!!!

-Ann P.

I’m a busy single mom with a demanding job. I was honestly so lost and had no idea or time to write a profile. I’m so grateful that I found The DIY Profile Kit. I love my profile now and it was super fast to write! Alyssa’s advice really helped me bring out my personality and humor. I’m getting some great matches and weeding out the guys who aren’t right. Thank you again!!

-Kady Davies

Working with Alyssa was a great experience all around. She is patient, intentional and has a great eye. I use her styling tips every day I get dressed and remember her professional advice when shopping!

-Katherine S.

Alyssa has such a great demeanor– very professional and engaging. She was calm and made me feel so comfortable during my Profile in a Day. From the initial phone conversation, throughout the entire process, has been an overall great experience. Her team is just as wonderful and a great group of women and professionals! Everyone made me feel super comfortable and excited! My photos and profile came out wonderful!

- A.M.

When I was ready to start dating after separating from my husband I was somewhat terrified and completely clueless about the dating app world. Alyssa helped me set up all my profiles advising me on which photos to use and what to say in my bio. And she shared so much of her own experiences which was so helpful in navigating this new landscape. I am so happy I connected with her. She’s my dating guru!

-K.K.

There has definitely been a big improvement for me with online dating. In fact I’ve matched with so many people I’m interested in meeting I’ve had to pace myself! I’ve had some great dates and am continuing to explore. Thanks for all your expert feedback and the boost of confidence that resulted from talking this all through with you!

-Heidi Ross

Alyssa is an excellent stylist. She effortlessly works within your price range and personal needs. She improved my wardrobe (and my style) immensely, and she’s a pleasure to work with.

-Courtenay O.

Building a dating profile was intimidating after my divorce, coming out of a relationship which started pre apps – but Alyssa was invaluable in helping me do everything from writing my bio to selecting my best photos and giving advice about the whole process. I got so many matches I barely had enough time in the week to schedule dates! No matter what your age, Style My Profile is the best at helping you navigate modern dating!

-Ronald J.

With The DIY Profile Kit, I felt much more confident putting up my profile. I’ve now been dating and one guy even said it was definitely my profile that hooked him!!

-Beth K.
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