You made your case like a lawyer. Stable job. Good guy. Ready for something real. All true. All irrelevant.
She weighed your points, nodded along, felt nothing — then fell hard for some tattooed bartender with a motorcycle and a gambling problem.
Logic is where attraction goes to die. The "22 Rules" work a level deeper, on the subconscious switches that decide within minutes whether you register as a MAN or as part of the furniture.
Stop presenting evidence. Start flipping switches.
Attraction runs on a clock.
She flirted for weeks. Touched your arm. Found reasons to be alone with you. And you were careful. Respectful. Waiting for the right moment.
The moment had a shelf life. It expired around month two, and by the time you asked her out, she'd quietly filed you under "little brother."
One of the hardest lessons inside the 22 Rules: women rarely wait. Interest either grows or it decays, and nothing decays it faster than a man who never moves.
Make the move while she's still inventing reasons to be near you.
What do you mean by getting back into shape? What is your objective? Once you define your objective do some introspection and figure out why you got out of shape. If you have access to weights then the LP program that Money & Muscle posted is solid and will suit most men. IMO, if your objective is to lean out and build muscle and strength I would drop the running for now. Running and lifting are antagonistic to one another. I would do a brisk walk or ruck before lifting. If you love running do it on an alternate day and no longer than 15-20 minutes in the upper ranges of heart rate. If you insist on running you will need to up your food and protein intake. But, resistance training and diet are superior to optimal body composition.
What is your height and weight currently? 1RPM on Squat, Bench, Deadlift?
Next Monday you'll feel more confident. After the gym you'll feel more confident. After one more drink you'll feel more confident. After you get a better haircut, a better jacket, a better job.
You've been "getting ready" for two years.
She's standing ten feet away right now. She'll be gone in four minutes. No amount of preparation will manufacture the courage that only comes from moving your feet.
Walk over. Stumble through the first sentence. Let it be clumsy. Let it be imperfect. You will feel more alive in those ten seconds than you have all month.