I’m Kayla, and yes, I’m that friend who tests stuff for real. I read a bunch of dating books for men this year. I tried the tips with two guys I help—my cousin Leo and my friend Max—and I also watched how those moves felt on my own dates. Some advice helped right away. Some felt weird. A little even backfired.
If you want the full blow-by-blow of that reading marathon, I unpacked every title in a separate Sharpman deep-dive you can skim right here.
You know what? A few simple changes made the biggest difference. Not magic. Just clear, kind, and brave.
Let me explain.
Quick context: Who I tested with
- Leo, 31, software engineer, shy on first dates, sweet once you know him.
- Max, 36, sales, fun and loud, tends to rush things.
- Me, 33, I date, I text, I notice what lands. I also sit there with a latte and watch people fumble through small talk. It’s kind of my sport.
We used Hinge and Bumble. For anyone who’s aiming more for a low-pressure, no-strings-attached meetup than a slow-burn romance, you can skim the straight-talk guides over at PlanCulFacile—they spell out how to set clear expectations, stay safe, and avoid mixed signals when you just want a hassle-free casual date. If you’re reading from Ontario’s Limestone City and want to shortcut straight to people who also prefer easy, drama-free connections, check out Kingston Hookups—their local-only listings let you quickly see who’s available tonight and what they’re looking for so you can meet up without the endless swipe parade.
“Models” by Mark Manson: Best for being real, not slick
This one surprised me. It pushes honesty. Not tricks. (If you’re curious, you can read more about the book on Mark Manson’s own page here.)
What we tried:
- Profile tune-up: one clear face shot (daylight, no hat), one full-body shot, one hobby shot. Leo used a climbing wall photo and a Sunday pancakes pic. No group shots as the lead.
- Simple ask: offer two times and a place. No “whenever works.”
Real example:
- Leo texted, “Wednesday 6 at Blue Bottle or Saturday 10 at Juniper Park? Coffee + a short walk.”
Mia picked Wednesday. They met. Forty-five minutes. Second date set.
What worked:
- The two-option ask cut the back-and-forth. It felt easy to say yes.
- The vibe was calm. Not needy. Not cold.
What didn’t:
- If you overshare too soon, it can feel heavy. Leo once talked about a past break-up on date one. Too much, too early. Save that.
Verdict: Great base book. Teaches you to act like yourself, but clear.
“Attached” by Amir Levine and Rachel Heller: Best for spotting patterns
I used this to label vibes. Not to label people.
What we tried:
- Leo wrote a short “how I date” note for himself: “I like plans. I need a little time to warm up. I check in daily but I’m not on my phone at night.”
- On date two, he said, “I like a plan for next week. I feel better when things are on the calendar.”
Real example:
- He and Kara set Thursday 7 pm sushi before they left date one. No vague maybes. They both relaxed.
What worked:
- Clear talk about pace kept the worry down.
- It stopped the “Is she into me?” loop, which eats your brain at 2 am.
What didn’t:
- Don’t play therapist. Max once said, “You’re anxious, right?” She was not amused. Keep labels to yourself. Speak for you.
Verdict: Use it to understand yourself, not to diagnose dates.
If you’re also juggling church community expectations while you date, the field notes from my faith-focused experiment live in this piece.
“No More Mr. Nice Guy” by Dr. Robert Glover: Boundaries, not bravado
Parts of this felt harsh. But one piece helped a lot: ask for what you want, with care.
What we tried:
- No over-texting. No “Just checking in again!” walls.
- Clear ask, clean no.
Real example:
- Max sent, “Loved the banter. Want to meet? Thursday 7 at Bar Flora or Sunday 3 at Beacon Park?”
She chose Sunday.
Another time, he said, “I can’t do late nights. 10 pm is too late for me.” She said, “Fair.” They picked 7:30.
What worked:
- Boundaries read as steady, not mean.
- It saved time. Big win.
What didn’t:
- If you mix this with cocky talk, you come off as a jerk. Keep the kindness.
Verdict: Good for backbone. Use a soft tone.
“How to Not Die Alone” by Logan Ury: Best for systems and photos
This one is practical. It gave us easy moves. (Logan Ury’s publisher page for the book is here if you want the official rundown.)
What we tried:
- Photo rule: face, full body, hobby, and a candid with friends (but not first). No car selfies. No fish.
- First date rule: 45-minute coffee or walk. End on a high. Set date two right there if it feels good.
- Decision rule: After two dates, choose yes, no, or hold for one more. No seven-week limbo.
Real example:
- Leo used iPhone portrait mode by a window. A friend took the pics. He matched more the same week. Like, a lot more.
Need a quick crash course on looking camera-ready? The concise grooming and style guides at Sharpman can help before you snap that first profile pic.
For everything that happens after that first coffee—how to plan, pace, and nail the follow-up—I mapped out my second-date playbook right here.
What worked:
- Short first dates cut nerves. You leave happy, not fried.
- The rules removed guesswork. Less spin. More action.
What didn’t:
- If you treat dates like a checklist, it feels cold. Smile more. Ask one playful question.
Verdict: Best for quick wins and momentum.
“The Game” by Neil Strauss and “The Art of Seduction” by Robert Greene: I don’t recommend as a core guide
I read them. I tried light pieces. Some banter helped Max. But a lot felt fake or mean.
Real example:
- Max teased a woman’s “basic fall boots.” She laughed, then cooled off. He got a tight smile and a quick exit. Not worth it.
If your grand plan is to open at the squat rack, see what actually worked (and bombed) when I stress-tested gym approaches over here.
What worked:
- A tiny bit of playful back-and-forth can be fun. Keep it warm.
What didn’t:
- Negging. Scripts. Power games. People smell it. I felt it too, and I wanted to leave.
Verdict: Skip. Or read as history, not a plan.
Small experiments that worked fast
- The two-option ask: “Tuesday 6 at Roam Coffee or Saturday 10 at the farmer’s market?” Simple yes.
- A 45-minute cap: “I have a hard stop at 7.” You can always extend if it’s great.
(That humane time limit grew out of a brutal night of three-minute rounds—my speed-dating survival story is here.) - High–low–why: “What was the high of your week? The low? Why?” It beats “So what do you do?”
- A kind wrap-up text: “That was fun. I’d like to see you again. Thursday work?” Clear is kind.
Real note I sent after a good date:
- “I had fun hearing your New Orleans stories. I’m free Thursday after 6. Want tacos at Lita’s?”
He said yes. Tacos were great.
What flat-out flopped
- Copy-paste openers. I saw the same “What’s your go-to karaoke song?” ten times in one month. I answered once.
- Late-night “wyd” texts. It sets the tone you may not want.
- Over-sharing trauma on date one. Keep it light, but real. Save the heavy for later.
One real week, numbers and results
- Leo matched with 9 people on Hinge after new photos. He sent 6