I have a 6-figure career (goal is to make it 7 before I retire), which also requires me to wear a suit and tie. My suits are tailored, and I wear some fairly expensive luxury brand accessories, like neckties, shoes, briefcases, watch etc. I'm not bragging here -- it's important for my line of work to brand yourself as competent and successful.
It's quite easy to not become a gold-digger's target, by sticking to this basic itinerary:
1. I show up on most dates after work, still wearing a suit. It's an instant DHV. Your margin for errors is considerably widened when you're wearing a tailored suit (not something baggy, out of style, or black). You are treated with respect by strangers. Service people are slightly intimidated by you, and when you're warm and friendly to them, that's alpha as fvck. Women love it.
2. When asked what I do, I always answer "I work at Men's Wearhouse." It's good for a quick laugh. If she insists on asking again, I tell her what I do, then immediately change the subject. I don't like talking about work on dates, or with anyone I don't work with. If she asks "how much do you make?" my answer is "more than you, don't worry" and I know the date is probably ending after the 2nd round of drinks-- usually because contrary to movies and popular culture, very few women are obnoxious enough to ask that question on a first date if they want you to like them. It means she's not that interested in you.
3. First dates are always at a bar for drinks. Never dinner. Never coffee. Never anything but at a bar for drinks. I usually pick an upscale pub, not anything exclusive or that's clearly chosen to impress a woman. I pick a place that has Yuengling on tap and has a basic bar menu for appetizers. No place with $20 c0cktails. I order Tito's and club so I can nurse it and not get my motor running to quickly.
4. I buy the 1st round. If the conversation is going well, I'll put the 2nd round on my tab also. Yep, dating costs money. Usually at this point, I'll know whether it's going well or not. If it is, I'll order appetizers, or simply ask "I'm hungry, want to get a bite with me? There's a great place down the street." Sharing food and booze is a human bonding activity that spans eons of humanity. No need to fix what isn't broken.
5. I then pick a simple, casual restaurant with entrees $10-20 range. Order a round at the table, keep the conversation flowing. When the check comes, I take it. I'm the man. I'm leading, I'm in charge, I'm responsible. I pay. And it's only a $40-50 tab max. If she follows you to a restaurant and offers to split (she often will), the date is usually going well -- although insisting on splitting the bar tab at the 1st venue can be a sign that she doesn't want to be taken care of by you, and it often not a great sign. It really depends on the girl.
6. After dinner, I suggest one more bar. I pick a quiet, dark lounge. Either on the way there, or there, I go for the kiss. The rest is history.
So the key is to pick the venues. Have total control over the itinerary. If she wants to go someplace expensive, go. But when the bill comes, tell the server directly "we're splitting this." Don't even clear it with your date. You pick, you pay. She picks, she pays.
