How to Decode the Art of Online Dating

Whether you’re newly divorced and finally feeling ready for a partner again, or you’re much new to the love department, online dating can feel daunting. How do you design an inviting profile? and authentic? And what about those dreaded photos? One thing is certain: there is clear a lot to consider, so we call in an expert.

New York-based personal stylist and dating coach Alyssa Dineen found love through online dating after a divorce, which she writes about in her book The Art of Online Dating. With clients in their 20s to 80s — in locations across the country (thanks, Zoom!) — Dineen guides them through the creation of their profiles and even helps them style and arrange professional photoshoots to capture those all-important dates -App Pictures. Below we asked Dineen to give us her expert advice on this often tricky task. Read on for every detail.

Oprah Daily: Why Are Many People Nervous When Starting Online Dating?

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alyssa meal: When I got into it, I didn’t know what I was doing and I had no one to turn to. All my friends were still married. I had a few single friends who had been online for a long time. For her, it was just, “Oh, you just created a profile. It’s no big deal.” I think you’re forgetting how there are all these nuances!

Coming from a photography and fashion background, it was pretty easy for me to figure out which photos work. Writing the bio—knowing what to write—required a lot of trial and error. Then you get to the actual part where you uploaded your profile and it looks great – but then you actually have to message people and set them up on a date.

Figuring all that out and forcing myself to date new people and keep an open mind turned into a fun social experiment on the side. At some point I met my partner. We’ve been together for over five years. When I met him and he found out I’m a stylist and art director, we talked about how I could help other people like us: people who are new to online dating – especially people our age and older, 35 and above. You didn’t grow up with that [it] may be completely new territory if you are either coming out of a long relationship or marriage. I wrote the book The Art of Online Dating, as a guide to help people like me and my boyfriend get ahead of the learning curve and into actual dating.

What advice do you have for people who are really nervous about trying dating apps?

one One important thing for people starting from scratch is to ask around. When I did it was more of a taboo than not talking about your online dating. And now it’s so different. Getting to the point where you can ask friends for advice or ask around with people who may be younger than you is the first step.

Once you’ve achieved that, there’s loads of research and things to read about. I have courses to help you get your profile up and running. A lot of people come to me with resistance, like, “Well, I really don’t want to go on an online date, but everyone says I have to.” You have to get out of that mindset, because it’s really beyond that.

That’s life now, you know? And sure, you could still meet someone at the grocery store, and that’s amazing. But everyone is into online dating. If you really want to be proactive about meeting someone, that’s exactly what you need to do.

Do you have any advice for anyone who is looking to retire after a divorce but feels like the dating landscape has changed since their last date?

It’s changed so much. One thing that came to mind pretty quickly was, “Oh, so much dating is actually texting.” It really is so much about practice and getting used to it – communicating with people and deciphering texts.

I think so much of it is experience and getting out there and practicing. It took me so long to even get to the point where I could comfortably send back and forth and not overanalyze every little thing I wrote.

It took me a while to get to the point where I would actually just start questioning people themselves. People my generation and older, a lot of women aren’t comfortable with it yet. And that’s something I really push people to do. You gotta get outta there. You have to be proactive.

You gotta get outta there. You have to be proactive.

It almost sounds like dating apps can be fun!

I hope I conveyed that in my book: you can really have fun with it! It seems really daunting at first, but really, you just have to let go of control of it. And in the process, you get to know yourself just by talking to new people and telling your story.

The Art of Online Dating: Create your most authentic self and cultivate a mindful dating life

The Art of Online Dating: Create your most authentic self and cultivate a mindful dating life

The Art of Online Dating: Create your most authentic self and cultivate a mindful dating life

What’s the biggest misconception about dating apps?

First, that everything is negative and bad. I think so many people go into it and dread it like it’s a last resort. That just makes me so sad because it So it doesn’t have to be. And again I know it’s up and down; it’s not always super fun. But going about it as positively as possible and just knowing that it actually works… folks do meet online

I have clients in their 70’s who have met their next partner; in their 60’s, in their 50’s, in their 40’s, in their 30’s, in their – really, it can work for any age, which I find amazing. If you’re really into it, keep an open mind, it can actually work.

It’s weird for me when a 55-year-old comes up to me and says, “I’m too old. I shouldn’t…” I say, “Are you kidding me? I have an 85 year old wife who is out there. You can do that.”

If you’re really into it, keep an open mind, it can actually work.

A picture is crucial for your dating app profile. What are your top tips for great photos?

persons [in] my generation is not used to taking pictures of themselves. Even with what I do, I didn’t have photos of just me. It was either my kids or my husband or my friends. You didn’t really think about having photos of yourself. I really encourage clients to practice selfies – I talk about that in the book and I talk hundreds of selfies. They will probably delete the first 500!

You would be shocked how many people still only have one photo on their profile. And they’re okay with that. Little do they know you need five or six or seven or more depending on the app. I talk a lot about how to style for your photos and keep it a little simple. And make sure you have clear, waist-high photos, no sunglasses.

What details should our readers add to their dating app profiles?

Staying away from negative statements on your profile is hugely important because a lot of people tend to do that — like, “Not looking for drama.” Just really keep people positive.

They also need to be unique and stand out. You can’t just write, “I like yoga and going out to restaurants and red wine.” You have to think of the most unique things about you. Instead of just “I like to travel”, be specific: “I like to travel [this] because of a certain place This and This.”

Let’s say our reader is getting ready for their first date with someone they met online. What’s your styling secret to making someone feel confident on a first date?

Don’t reinvent the wheel every night when you go out on a first date. Just pick an outfit that makes you feel great and you know you look good in it. When you walk out the door you will feel really confident.

This person has never seen you before. You can literally wear the same outfit every time. And it’s your go-to place, and you know you’re feeling good, your shoes don’t hurt, you’re not messing with your shirt, your pants aren’t too tight… Taking that out of the equation is huge because on a first date everyone is so nervous.

This interview has been edited and shortened for clarity.

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