I'm 32 and never played as a kid - picked it up at 27, but I was a college athlete, and I'm about as athletic now as I've ever been, which is a big part of my game.

Background: I live in NYC (near Central Park courts) and Florida (for long periods during the winter) and have a very flexible schedule. It can be hard to find court time and hitting partners at the hours the courts are available, but have met a few guys who I play with ~1-3 times a week via a Slack group.

Skill level: Probably a 3.75-4.0... I win about 30-40% of games vs people who call themselves 4.0. Never played USTA or a tournament, so season that rating however you like. Singles is what I actually care about.

I'm decided I'm in a position to put $2-4k a month toward this, and make tennis a top-three life priority. Goal is 4.5. I'll say 5.0 out loud even though I assume some of you are about to explain why that doesn't happen for someone who started at 27 - I'd rather hear it now than find out in four years.

If it were your money, where would it go? The allocation interests me more than the total.

What I can't weigh:

• Buying court time and a standing hitting partner. Is paying a pro to just hit with me three mornings a week the highest-value thing on this list? Cheaper than lessons and it solves my actual problem of finding people/court time.
• Privates - how many a week before it stops compounding? One great coach weekly, or three sessions with whoever's free?
• How do you spot a good coach early? I keep reading about guys who spent two years getting their follow-through fixed while their footwork stayed broken.
• Clinics and drill groups vs. privates for a singles player
• Camps - real training or a vacation with rackets?
• USTA leagues, flex leagues, tournaments. Never done any of it and I want to. How much does competing move you compared to more practice? I've heard ladders and such in the city are pretty painful, but Florida is prob a lot easier.

Already have a Slinger and the time to use it, but find I end up just hitting a bunch of good repeat shots that don't really translate to matches. Maybe I need to change it up.

Most interested in adult learners who got to 4.5+ in singles, or people who went all-in and found the ceiling. NYC-specific answers very welcome - courts, coaches, leagues, whatever you'd do differently knowing what you know. And if the answer is that the money mostly buys me a schedule and the rest is reps, say that.

Note: I posted this a week ago, but despite getting positive reviews, Reddit's filters took it down with no reason cited (maybe the links?), but I'm trying to post again. Enjoy!

I'm a guy who has never even attempted to venture into the world of beauty product gifting for my girlfriend in ~2 years of dating. She loves makeup and usually buys it on her own so this year I tried to surprise her. Seeing the foundation bottles scattered around, I figured I'd start there. How hard could it be?

Reader, it is unbelievably hard.

She has a bottle in her drawer I figured I'd just match. Squinted at the label, got the shade. Then she mentioned she "wanted to try something different." Cool. So now I needed a brand she doesn't already own.

I was a little intimidated to go to Sephora alone, so I googled "foundations like X" and learned about the whole industry of foundation matchers. So I tried every online shade finder I could find. By the end, I was almost interested in the space. I am sharing my findings and ranking by how useful each was to a clueless boyfriend for future clueless boyfriends.

1. Findation

Type in one shade you know fits, get a list of equivalents across ~200 brands. I had one shade off her bottle so it worked. Real gripe: the list it spits out is huge, and there's no clear signal for which one is actually the best match. Just ranked by some algorithm I can't see. Without a way to validate, you're trusting it. UI looks like 2009 which I respect.

2. ShadeTwin(dot)app (my personal favorite, see below)

Type a brand and shade, see actual TikTok creators wearing it next to whatever other brands they wear. No quiz. No selfie. You just look at people. My unsolicited tech advice: would be better if you could enter multiple shades she's worn and have it triangulate... like, narrow the recs to brands that overlap across all three bottles in her drawer. Coming back to this in the verdict below. a

3. Sephora Color IQ

Face scan in store with their device. Cool concept/tech, but obviously can't do this without her. Pass.

4. Temptalia Foundation Matrix

Cross-referenced database of basically every foundation shade ever made. Not a finder, an encyclopedia. Cool for makeup nerds. For me it was like reading chemistry to make toast.

5. Maybelline Perfect Shade Foundation Finder

Selfie + questionnaire, suggests Maybelline only. The tool is a vending machine. The vending machine sells Maybelline.

6. Perfect Corp / YouCam

AI photo upload. Rendered her face in a tone that read vaguely Mediterranean. She is not Mediterranean. Closed the tab.

The verdict

1st Place: Shade Twin It was visual so it was extremely helpful for me. Every other tool either makes you guess on someone else's behalf, only shows you one brand, or hands you a list with no way to tell which option is actually best. None of that survives being a clueless boyfriend.

Shade Twin's whole thing is real people on TikTok. If someone with her skin tone wears her bottle AND another brand in the same video, that's the answer. You just look.

2nd Place: Findation: Second because the data is comprehensive, but the unranked-list problem made it hard to commit to a single pick. Brand-locked ones (Maybelline, Sephora, Color IQ) only help if you've already picked a brand, which I had not.

If anyone has actually cracked this, tell me before next birthday 🙃.

I'm a guy who has bought my girlfriend zero beauty products in ~2 years of dating. She loves makeup and usually buys it on her own so this year I tried to surprise her. Seeing the foundation bottles scattered around, I figured I'd start there. How hard could it be?

Reader, it is unbelievably hard.

She has a bottle in her drawer I figured I'd just match. Squinted at the label, got the shade. Then she mentioned she "wanted to try something different." Cool. So now I needed a brand she doesn't already own.

I was a little intimidated to go to Sephora alone, so I googled "foundations like X" and learned about the whole industry of foundation matchers. So I tried every online shade finder I could find. By the end, I was almost interested in the space. I am sharing my findings and ranking by how useful each was to a clueless boyfriend for future clueless boyfriends.

1. Findation

Type in one shade you know fits, get a list of equivalents across ~200 brands. I had one shade off her bottle so it worked. Real gripe: the list it spits out is huge, and there's no clear signal for which one is actually the best match. Just ranked by some algorithm I can't see. Without a way to validate, you're trusting it. UI looks like 2009 which I respect.

2. Shade Twin (my personal favorite, see below)

Type a brand and shade, see actual TikTok creators wearing it next to whatever other brands they wear. No quiz. No selfie. You just look at people. My unsolicited tech advice: would be better if you could enter multiple shades she's worn and have it triangulate... like, narrow the recs to brands that overlap across all three bottles in her drawer. Coming back to this in the verdict below.

3. Sephora Color IQ

Face scan in store with their device. Cool concept/tech, but obviously can't do this without her. Pass.

4. Temptalia Foundation Matrix

Cross-referenced database of basically every foundation shade ever made. Not a finder, an encyclopedia. Cool for makeup nerds. For me it was like reading chemistry to make toast.

5. Maybelline Perfect Shade Foundation Finder

Selfie + questionnaire, suggests Maybelline only. The tool is a vending machine. The vending machine sells Maybelline.

6. Perfect Corp / YouCam

AI photo upload. Rendered her face in a tone that read vaguely Mediterranean. She is not Mediterranean. Closed the tab.

The verdict

1st Place: Shade Twin It was visual so it was extremely helpful for me. Every other tool either makes you guess on someone else's behalf, only shows you one brand, or hands you a list with no way to tell which option is actually best. None of that survives being a clueless boyfriend.

Shade Twin's whole thing is real people on TikTok. If someone with her skin tone wears her bottle AND another brand in the same video, that's the answer. You just look.

2nd Place: Findation: Second because the data is comprehensive, but the unranked-list problem made it hard to commit to a single pick. Brand-locked ones (Maybelline, Sephora, Color IQ) only help if you've already picked a brand, which I had not.

If anyone has actually cracked this, tell me before next birthday 🙃.