Dear Gabby

The Gabber’s semi-regular advice column, Dear Gabby, is here by reader demand. Have a question or a conundrum for Gabby? There’s no problem too small for our resident advisor. Send your questions – they can be anonymous – to deargabby@ thegabber.com.

I’ve lived in my house now for about five years. I love my neighborhood and I always wave to the neighbors – the trouble is I’ve never really met them! I always meant to introduce myself when I moved in, but five years on.... It seems a little late for that. Will they think I’m weird if I do it now? What do you suggest?

You know what would be weird? If your neighbors were thinking the exact same thing! What if they are thinking how weird they’d seem if, after all these years of waving and smiling, they wanted to finally meet? Then, you both are going into a sixth year, waving and smiling and secretly fearing being weird if you introduced yourselves. Let’s dismantle the secret, and most likely nonexistent, weirdness. If it’s on your mind and heart to introduce yourself, go for it! I imagine steps toward more kindness, more community and more friendship are more welcome than they’ve ever been before.

I’m seeing someone I met on a dating app about a month ago. Things are going well, considering we live in plague times, but I’m running out of date options! Neither of us are comfortable going to restaurants, so we’ve been cooking at our homes, and doing take-out. But we’d like to go out somewhere… What are some of your best ideas for “outdoor” dating?

you two graduate to long road trips). You can make a list of all the ones that sound or look interesting, then get to planning those dates. You can be active and do a hike or walk. You can even take something you would do indoors like a puzzle or board game to play at the park. Whether you both meet up to walk, hike, picnic lunch, play a game or even just meet for a romantic sunrise or sunset outing, let Florida’s natural beauty be a backdrop to memorable conversation, unique sights and fun moments of togetherness.

I’ve been at the same job at a bank for 15 years. The pay is very good, and the benefits are too. The problem is, I am burned out and I’m starting to hate it. Recently I got the opportunity to interview for a total dream job at a nonprofit. The only problem is it’s a lot less pay. I don’t have any kids, and I could probably swing the pay

cut, but it will be stressful, and require some life changes. Do I go for it or play it safe?

I had a whole other career before becoming a writer. I was a consultant for a large technology firm. The pay was excellent. The benefits out of this world. I had a corporate AmEx card! Yet, my heart wasn’t in the work. I yearned for a life doing the thing I love most in the world: writing. I quit that consultant job in 2005 and haven’t looked back. Sure, I could be making more money, and life as a writer is less “secure” than a corporate gig. But I’ve never been happier. Happiness is the part of my life that I have deemed non-negotiable. I can put limits on my spending, but I do not want to put limits on my joy. Ask yourself where you’d be most happy, where you’ll get the most fulfillment, and lead with joy. If it means taking a risk on yourself, go for it. My Pops would call that “betting on a winner.”