Relationship Coaches Answer Your Messiest Dating Questions

By
Cameron Harvey
August 22, 2025
9
min read

Ever notice how dating advice online feels like it was written by someone who's never actually been on a messy first date? 😅 Like, sure, "just be yourself" sounds great in theory, but what happens when "yourself" accidentally mentions your ex three times in one conversation or spills marinara sauce on your white shirt?

Here's the thing - real dating is messy, awkward, and full of those moments that make you want to hide under your covers forever. That's exactly why I reached out to actual relationship coaches who've heard it all. And I mean all of it.

These aren't your typical "smile more" tips. We're diving into the questions you're actually googling at 2am, the ones that make you wonder if you're the only person who has no clue what they're doing. Spoiler alert: you're not.

When Physical Chemistry Feels One-Sided

"I'm super attracted to them, but I can't tell if they feel the same way. How do I know without making things weird?"

Dr. Sarah Chen, a licensed relationship therapist, gets this question constantly. "Physical attraction isn't always obvious," she explains. "Some people are naturally touchy, others show interest through sustained eye contact or finding excuses to be close to you."

But here's what I've learned from my own dating disasters - sometimes you just have to take the temperature check. Not in a creepy way, obviously. Try the subtle touch test. A hand on their arm during conversation, sitting a bit closer during a movie. Their response (or lack thereof) will tell you everything.

The key is paying attention to reciprocation. Do they lean in when you get closer? Touch you back? Or do they subtly create distance? Trust your gut on this one.

The Dreaded "What Are We?" Conversation

Ah, the conversation that makes everyone break out in a cold sweat. You've been seeing each other for weeks, maybe months, but nobody's defined anything. It's like relationship limbo, and frankly, it's exhausting.

Relationship coach Marcus Williams has a refreshingly direct approach: "Stop making it bigger than it needs to be. You're not asking them to marry you - you're just asking where you both stand."

Here's a script that actually works: "Hey, I really enjoy spending time with you. I'm curious about what you're thinking in terms of where this is heading." Simple, direct, no pressure.

The worst thing that can happen? They're not on the same page, and you find out sooner rather than later. That's actually a win, btw. Better to know now than waste months wondering.

When They're Still Active on Dating Apps

This one hits different. You're developing feelings, but their dating profile is still getting updates. It stings, ngl.

"This is where boundaries become crucial," says Dr. Chen. "You can't control their behavior, but you can decide what you're comfortable with."

Some people keep apps as a safety net until things become official. Others genuinely aren't ready to focus on one person. Both are valid, but you deserve to know which situation you're in.

Sexual Compatibility Red Flags Nobody Talks About

Let's get real about the elephant in the room - sexual compatibility matters. A lot. But nobody teaches you how to navigate those early conversations without feeling like you're conducting a job interview.

Dr. Lisa Rodriguez, a certified sex therapist, emphasizes that sexual compatibility goes way beyond physical attraction. "It's about communication styles, comfort with vulnerability, and aligned values around intimacy."

Red flags to watch for early on? Someone who can't have mature conversations about physical intimacy, makes you feel judged for your preferences, or pressures you to move faster than you're comfortable with.

Green flags? They check in with you, respect your boundaries, and can laugh when things get awkward (because they will, and that's totally normal).

The Pressure to Define Your "Type"

Here's something that used to stress me out - feeling like I needed to have a clear "type" or specific preferences figured out. Plot twist: it's totally okay to be figuring it out as you go.

"Sexual identity and preferences can evolve," explains Dr. Rodriguez. "What matters is staying curious about yourself and communicating honestly with partners."

Don't let anyone pressure you into boxes that don't fit. Your journey of self-discovery is yours to navigate.

When Past Relationships Keep Showing Up

We've all been there - you're having a great time with someone new, and suddenly your ex's ghost decides to make an appearance. Maybe it's a random text, maybe it's just your brain playing tricks on you.

Relationship coach Angela Torres sees this constantly. "Healing isn't linear, and sometimes old wounds get triggered by new connections. The key is recognizing it and not letting it sabotage something good."

Some practical advice? Be upfront if you're still processing stuff from your past. Most understanding people will appreciate the honesty. And if they don't? That tells you something important about their capacity for empathy.

Comparing New Partners to Exes

This mental trap is so common it should have its own support group. Your new person does something differently than your ex, and suddenly you're spiraling into comparison mode.

"Comparison is the thief of joy," reminds Torres. "Every relationship is different because every person is different. That's the point."

Try to catch yourself when you notice the comparing starting. Ask yourself: is this a legitimate concern about compatibility, or am I just scared of something new?

Digital Dating Dilemmas

Modern dating comes with a whole new set of complications that our parents never had to deal with. Social media stalking, read receipts, the anxiety of waiting for texts back - it's a lot.

"Technology has created artificial urgency around communication," notes Dr. Chen. "Just because someone can respond immediately doesn't mean they should or will."

Some boundaries that actually help: Don't over-analyze response times. People have lives, jobs, and sometimes their phone dies. Revolutionary concept, I know.

Also, resist the urge to deep-dive their social media history. That photo from 2019 with their ex isn't relevant to your current situation, and it's only going to make you feel worse.

The Screenshot Dilemma

We need to talk about the group chat screenshot situation. Yes, your friends want to help analyze their texts, but sharing private conversations without consent isn't cool.

Better approach? Talk about your feelings and concerns without sharing actual messages. Your friends can still offer support and perspective without violating someone's privacy.

FAQ: Your Most Googled Dating Questions

How long should I wait before having "the talk" about exclusivity?

There's no magic timeline, but most relationship experts suggest having this conversation when you find yourself wanting to know where you stand. Could be three dates, could be three months. Trust your instincts.

Is it normal to feel anxious about someone I really like?

Totally normal. When we care about the outcome, anxiety often follows. The key is managing it so it doesn't sabotage the connection. Deep breaths, friend.

Should I bring up sexual health and testing early on?

Absolutely. It might feel awkward, but it's a sign of maturity and respect for both of your health. Most adults appreciate this conversation, even if it feels scary to initiate.

How do I know if I'm being too picky or not picky enough?

This is about knowing your non-negotiables versus your preferences. Non-negotiables are things like respect, honesty, and shared core values. Preferences are things like height, job, or hobbies. Be flexible on preferences, firm on non-negotiables.

What if I'm developing feelings but they seem more casual about everything?

This mismatch happens more often than you'd think. The only way forward is honest communication. Share how you're feeling and ask about their perspective. You deserve to know where you stand.

Red Flags That Deserve Your Attention

Let's talk about the stuff that should make you pause and really think. Not every red flag is a dealbreaker, but they're all worth paying attention to.

Someone who consistently makes you feel like you're asking for too much when you express basic needs? That's not great. Someone who can't handle any feedback or gets defensive about everything? Also concerning.

Dr. Williams emphasizes watching how people treat service workers, talk about their exes, and handle stress. "These moments reveal character in ways that planned dates never will."

Trust your gut. If something feels off, it probably is. You don't need to have concrete evidence to honor your instincts.

Building Confidence in Dating

Here's something I wish someone had told me earlier - confidence in dating isn't about being perfect. It's about being comfortable with who you are, including your quirks and imperfections.

"Authentic confidence is magnetic," says Torres. "It's not about having all the answers. It's about being curious, kind, and genuine."

Some practical confidence boosters? Know your worth outside of dating. Have hobbies, friendships, and goals that fulfill you. When dating becomes just one part of your life instead of the main event, the pressure decreases significantly.

Also, remember that rejection isn't personal. Sometimes people aren't in the right headspace, sometimes there's no chemistry, sometimes timing is off. None of that reflects your worth as a person.

Final Thoughts

Dating is messy because humans are messy, and that's actually kind of beautiful. All those awkward moments, miscommunications, and "did I really just say that?" experiences? They're part of the process of finding someone who gets you.

The relationship coaches I spoke with all emphasized the same thing - there's no perfect formula for dating success. What works is being honest about what you want, communicating clearly, and staying true to yourself even when it feels scary.

Your dating journey doesn't have to look like anyone else's. Some people find their person on the first try, others go on fifty first dates before finding their match. Both paths are completely normal.

Remember, you deserve someone who's excited about you, not someone you have to convince to care. The right person won't make you feel like you're too much or not enough - they'll make you feel like you're exactly what they've been looking for. ✨

Keep being brave enough to put yourself out there. The messy, imperfect, beautifully human experience of dating is how we find our people. And tbh, the best relationships often start with the messiest beginnings anyway.