Your Top 25 Dating & Relationship Questions Answered

Your Top 25 Dating & Relationship Questions Answered

Part of the reason I created this blog was to answer every one of the dating and relationship questions I ever asked Google when I was at my lowest.

And because the common denominator of healthy relationships is intact self-esteem, the root of my obsessive and very specific questions was always:

  • Finding a cure for feeling like I was never enough.
  • How to stop my obsession with winning and being chosen. I was always in some sort of passive competition to be chosen by a toxic person. And when you’re in a position of someone having to choose you, you come to the relational table without any leverage. The requirement of being able to stay at that table then becomes handing over your dignity to the person across from it.
  • How to stop being affected by every.single.blow of the emotional and relational breeze.
  • How to be confident enough to not only listen to but act on my instinct instead of prosecuting it to death.
  • How to run out of f*cks to give when it came to my fears, insecurities, and just put an end to my unlucky-in-love “streak” – which had become a fancy word for “life.”
  • How to stop always being at everyone else’s emotional beck and call when no one was ever at mine.

Through the years, I’ve been asked so many dating, self-esteem, and relationship questions from men and women that I’ve written about at length. I don’t ever write from any sort of psychological high horse. I’m human and I’m fallible. I still get painfully insecure, massively triggered, and I make mistakes every day.

The only difference between now and then is that I allow these things to be the experiences that they are instead of definitions to subscribe to. I no longer attract circumstances and people who affirm that subscription because I have unsubscribed.

I write to solidify what I’ve learned from the mistakes I’ve made so that I can help as many people as possible. I also write to remember my own advice.

I wanted to address 25 of the top dating, self-help, and relationship questions I’ve been asked through the years.

So here they are…

Your top 25 dating and relationship questions answered.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #1: How do you deal with mutual friends/your ex’s family after a breakup?

Mutual friends and your ex’s family are tough because it’s essentially like meeting with/talking to your ex. In many ways, it’s the closest you can get to your ex. There’s a connection there and whether they report back to your ex or not, these relationships can be very painful to maintain after a breakup when you are at your most paranoid, heartbroken and sensitive. Bottom line: If these people are causing ANY kind of discomfort or anxiety for you, my best advice is to kindly distance yourself from them. No one is going to think that you’re weak and if they do, they’re just trying to soothe their own ego from the shock of you doing the one thing that they least expected: Respectfully drawing your own line in the sand.

Yes, they can be a great tactical instrument in getting revenge, a certain message across, information, etc., but people aren’t instruments to play. They’re not your soldiers to deploy nor should you ever be theirs. And your withdrawal is the classiest “revenge” there is.

These people have their own agendas, fears, angles, and loyalties that they may like to deviate from in the form of blurring boundaries. Stay in your lane – with blinders on – until you reach indifference.

The best revenge isn’t being BFFs with his brother and Mom – it’s not giving a f*ck.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #2: Should you be bothered/is it a deal-breaker if you start to date someone and they are still active on dating apps OR have their profile still open but aren’t active?

Yes, you should be bothered to an extent in the beginning because you are human and it’s normal. Just don’t act on that emotion right in the beginning or you will look nuts.

It’s only a deal breaker if:

  • They aren’t upfront – if they’re shifty and secretive about it. Especially if you’ve brought it up to them and they keep it up.
  • They claim that they are exclusive with you and don’t delete their dating profile. Even if they’re not active on the app, the fact that they still leave the profile open is not only hurtful and disrespectful, it’s an insult and a very immature deal breaker.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #3: Is it a problem if my partner is following a bunch of Instagram booty/boob models and likes the photos? What if he follows but doesn’t like the photos? What if he follows and/or likes straight-up porn?

In the realm of long distance relationships, the dynamics of social media can sometimes take center stage. Whether your friends and family are connected with him doesn’t hold as much weight as your own connection. If his online presence feels excessive and borders on disrespect, it’s essential to note that he might not be intentionally trying to harm or devalue you. Rather, his actions are revealing his relational values. And that’s a revelation you can act upon, deciding whether to stay committed or move on.

The only way out of being jealous/insecure-labeled is by acting on what you see. Never react to it and give someone (who has already proven to be empathetically compromised and completely fine with this kind of behavior) a map to your triggers, wounds, and insecurities.

Liking posts from these followed accounts is just taking it up to an even more obnoxious notch. I mean, is this really sexy to you?  This is a grown adult who knows how social media works and knows you can see these things. If you’re in a relationship with someone and he’s also following a bunch of trashy accounts that make you feel worthless, why can’t he at least just LOOK at the photos? This whole thing of actually taking the time to like a photo, knowing that everyone who follows him will see the like (including you), is as mindless as a dog pissing on every fire hydrant that they pass.

For me personally, I would never involve myself with a man who had these kinds of values in the first place. It’s all just too much. A lot of women justify it by “appreciating the transparency” and “at least he’s not doing it behind my back.” And that’s fine. All I ask for is what I give and the denominator of what I consistently give is r-e-s-p-e-c-t. I personally don’t want to go follow and like a bunch of dick pics. It’s not my thing. There’s no judgment, it’s just not my cup of tea.

I no longer value my anxiety to the delusional level of confusing it with passion.

You deserve an adult relationship, not some virtual competition of keeping up with whoever he’s double-tapping.

And if he’s following straight-up porn accounts and knows that you follow him… I’d say no thanks. Life is tough enough. There are enough distractions. If your partner is implementing his own distractions while giving you (and everyone who follows him) a front-row seat to it, it’s okay to leave the theater.

This is a red flag as far as a mutual relationship goes – the kind that you claim to want and know that deep down, you deserve. Take out the trash. Stop dumpster diving so that you have a license to complain about the filth.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #4: What’s the best way to make a long-distance relationship work?

Long-distance relationships can definitely work as long as, according to BOTH parties, the distance is temporary. Communicate clearly and always be honest. Be transparent, be real, be respectful, keep it spicy with FaceTime, sexting, and VISIT each other as much as possible.

It’s necessary to have a mutual end game as far as when/where there will no longer be physical miles between you.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #5: Can you fall in love with someone who you aren’t initially attracted to?

Yes. This isn’t about settling or forcing yourself to be with someone that you are physically repulsed by (there needs to be some level of attraction). This is about understanding yourself and your triggers to the extent that you make the commitment to embrace what’s good for you and flush what isn’t.

It took me a really long time to learn how to be attracted to what was good for me, instead of what triggered me. I’ve never looked back since.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #6: How do you trust yourself and your partner?

Without respect, there can be no trust and without trust, the only thing left to do is play little league games. Trusting yourself happens when you build respect for yourself.

Self-respect is established when you prove to yourself that you always have your own back. And that you consistently do so in spite of the magnetic pull that your head, heart, and libido has to what may feel great in the short-term but what will end up disabling your capacity to respect anything other than your triggers in the long term.

Same goes for building trust with your partner  – If someone is consistently inconsistent, there will be no genuine trust or respect – for them AND for yourself.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #7: What if you’re in love with your best friend who doesn’t want anything more than friendship?

If you’ve expressed your feelings and they’re still pushing the BFF card in spite of knowing how much you are hurting… you need to take a step back and cool your jets.

You also need to ask yourself how good of a friend they really are if they push the status quo while knowing that your heart is breaking.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #8: When should you have sex for the first time?

This is obviously, a very personal question that may be specific to your moral, religious, and cultural influences. For me personally, I always tell people not to give it a set amount of time. When you do that, you become more focused on hitting a mark of time than you are a mark of connection.

Focus less on time passing and more on connecting.

Have sex when you feel as though it’s mutual as far as feelings, values, and standards go. You should feel safe, secure, respected, and connected with/to. For me, it’s more about when I feel that connection than how much time I have to wait so he doesn’t think x,y, and z. Always turn inward – what do YOU think?

Also – make sure that before you have sex in between the legs, you’ve had sex in between the ears with this person. Emotional and intellectual sex/connection is so important.

Anyone anywhere can go get laid but coupling that physical connection with one that was pre-established between the ears makes it that much more mind-blowing and intimate. Have sex between the ears first.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #9: Should you leave it to the guy to initiate contact?

This is a little too tactical for me. You definitely don’t want to initiate all contact. You never want to overload and emasculate your partner or play games.

Men love an intellectual challenge, not a communicative one.

They also love when women initiate contact. This should be two-sided.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #10: What if he has a lot of female friends?

It’s fine as long as they all know about you and have healthy boundaries.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #11: What if he always texts and rarely calls?

Red flag with too much shadiness to see any light. Fold immediately.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #12: How do you communicate that you’re not looking for a casual hookup?

By translating through your words and actions that you’ve been there, done that, and are looking for something substantial. If that scares the other person off, they’re not ready. Don’t tie your worth to getting a little league player to play at major league level just by taking him to an MLB game.

If they go along with it to get their needs met in the present moment, trust me when I say that there will be red and pink flags surrounding all of those accommodations. Know what you want, set your own standard and never settle

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #13: Can having sex too soon ruin the chances of a long-term relationship?

In my experience – at the right age with the right person, connection, communication, boundaries, and self-respect… I don’t think so.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #14: Should you only have sex if you are in an exclusive relationship?

This is a very personal question because it applies to your individual preference. Personally, I think commitment is key – Are they committed to being honest, communicative, valuing you, your health, and your emotional well-being?

If you have feelings for this person and know that if they slept with someone else you’d be crushed, you definitely need exclusivity to proceed.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #15: How do you handle seeing your ex and his new girl?

My wet bathing suit theory:

If you’re driving yourself up a wall, stalking every social media move of his new girl, I want you to think about this: Imagine you got a beautiful bathing suit and you put it on. You never quite felt comfortable or totally beautiful in it and it wasn’t constructed that well, but it grew on you and you loved it.

You wore it proudly the entire day – in the ocean, playing beach volleyball, in the pool, on the sand, on a boat, back in the pool, when you peed in the ocean, etc. You finally get home, still wearing it. The bathing suit is dirty and still damp. It’s got ocean water, chlorine, sweat, and SPF all mixed in. You feel gross from being in it all day, so you immediately take it off, hang it up on your shower rod and take a long shower to clean off.

WHILE you’re showering, however, a new girl comes into your bathroom and PUTS ON (so gross), the wet bathing suit that you’ve been swimming in, sweating in, peeing in (who hasn’t peed in the ocean?) and running around in all day.

She may look way better than you did in the bathing suit – She may be able to fill it out in all the right areas and make it look sexier and more expensive and valuable than you ever did BUT…

It’s STILL your wet, dirty, and USED bathing suit that she’s wearing. Gross.

When you social media stalk the new girl or run into her and your ex, have some empathy and be the class act that you are. Don’t hate on her. She’s wearing your wet bathing suit and has no idea how dirty it is. She just thinks it was wet because it came fresh out of the washer.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #16: Is flirting with another girl cheating?

I am so much less concerned about labeling this as cheating and so much more concerned with the circumstances and level of respect and communication on both ends. I’m not the jealous type AT ALL but I am always the respect type.


Forgiveness is nothing more than adjusting your boundaries in light of accepting who someone has revealed themselves to be.

If I came into your kitchen and touched a hot stove, I would immediately accept that I got a bad burn and adjust my boundaries to never touch a stove again. I wouldn’t think that the stove burned me because I wasn’t good enough and touch every stove in every kitchen I went into just to make sure I wouldn’t get burned again.

Stoves are not meant to be touched and cats meow, they don’t bark.

Accept that you met a cat who cried woof and adjust your boundaries to no longer dating cats that claim to bark. Cats MEOW.

Forgive your ex by adjusting your boundaries and letting him/her go in peace.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #18: How do you deal with your ex wanting to be friends after a breakup?

You don’t. Even if you dated the Dalai Lama, you still need to take the time to heal, deal, and process. If this person wasn’t a good friend to you in your relationship, trust me when I say that they will be a “friend” of very draining and diminishing returns outside of the relationship.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #19: What if my boyfriend still has a close relationship with his ex?

How close is close? I’ve dated men who were closer to an ex they dated for a few months than others who had children with their ex. If your partner and his ex do not have boundaries, FOLD. You will never be in a mutual relationship; always in a threesome. No thanks.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #20: What do I do if I’ve been ghosted? Did I do something wrong?

Unless you behaved like an obnoxious and abusive wild banshee, ghosting says more about the ghoster than it will ever say about the ghostee.

Follow up once and then be done.

Don’t ever waste time investigating why someone sh*t the communicative bed.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #21: Do you think it’s possible for a man to be in a long-term affair and still be in love with his wife?

This one is tough. My knee-jerk answer is “no.” I don’t have experience with this but I think it’s more about being in an obligatory/history/matrimonial/financial/guilt/comfort-induced idea of love and inverted safety than true love itself.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #22: How do I not carry the baggage from past toxic relationships into my current dating life?

Be classy, don’t audition, and remind yourself just how much you would hate for someone else to bring all of their moldy baggage into your relational house.

You work too hard to keep your house clean and you don’t have the room for that.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #23: What do you do if he won’t commit?

If he won’t commit to whatever it is you want him to commit to, you need to do the one thing he can’t do and speak with your actions. Fold.

YOUR DATING AND RELATIONSHIP QUESTIONS ANSWERED #24: What if he’s into things that I’m not into in the bedroom and makes me feel bad about it?

Red flag. What he’s wanting may be a red flag in and of itself, but the biggest red flag for me is the guilt-mongering for something that you’re not comfortable with doing. Keep your clothes on and fold.


You know you’re being needy when you put your fundamental needs in the hands of anyone other than yourself.

Written by: Natasha Adamo

If you’re looking for further and more specific help; if you’re tired of waiting to be chosen and ready to choose yourself, personalized coaching with Natasha Adamo is the answer. Book your one-on-one session today.

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Author of Win Your Breakup, Natasha Adamo

About Natasha Adamo

Natasha Adamo is a globally recognized self-help author, relationship guru, and motivational speaker. With over 2.5 million devoted blog readers and clients in thirty-one countries, she is a beacon of inspiration to many. Her debut bestseller, "Win Your Breakup", offers a unique perspective on personal growth after breakups. Natasha's mission is to empower individuals to develop healthier relationships and actualize their inherent potential.

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