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30 Dating Dilemmas in 30 Days – Part 2

Toyboy Warehouse is on a mission, we have 30 dating dilemmas from members past and current. We have 30 days to answer them.

To help we’ve enlisted the best and brightest in dating & relationship experts. They’ve kindly offered their unique insight to help us meet our target.

So, how did we do?

Rachel Astarte

Tell us about yourself

I am a psychotherapist, transformational life coach, author, and educator in the New York City area. I am the author of Celebrating Solitude: How to Discover and Honor Your Highest Self.

http://rachelastartetherapy.com

http://bit.ly/rachelastartebooks

http://bit.ly/celebratingsolitudepb

If someone came to you for dating/relationship advice, what should they expect?

A client interested in dating and relationship advice can be sure that we will begin with the only thing we can begin with: him- or herself. Development of the self is essential before we can enter into a relationship with another person.

What are some of the projects you’re currently working on?

Aside from seeing clients, I’m spending much of my time writing and producing my new podcast, Self Talk with Rachel Astarte (selftalkpodcast.com).

Dating Dilemmas

Name: Derrick

Age: 40

Gender: Male

“I’m about to become divorced? How difficult is it for a divorced guy to get back into dating. I’m starting to get nervous that things will be pretty difficult for me.”

Be sure you’re ready. Spend as much time as you need to get to know yourself—what you want and don’t want in the next relationship. Never feel pressured to get back into the dating world. When you are ready, you will know.

Name: Anonymous

Age: 39

Gender: Female

“What would you recommend for someone who’s really shy but would love to be dating?”

What does shy mean to you? Do you feel insecure about who you are or are you simply particular about the company you keep? If it’s the former, spend some time celebrating your life just as it is. There is no one exactly like you in all the world. That’s pretty amazing. Confidence in that knowledge is very attractive. If it’s the latter, accept that you will need to be discerning about the people you choose to date. Nothing wrong with that. Trust your instincts.

Name: Martin

Age: 21

Gender: Male

“I’ve never been on a proper first date in my life. I’ve had cougar girlfriends but I’ve never had an official first date. Help.”

It helps to think of dating as a kind of social club. Throw away all expectations of what you might want from the date, and settle into getting to know that fellow human being who’s chosen to spend time with you. That’s enriching all by itself.

Marissa Geraci

Tell us about yourself 

I am a Licensed Mental Health Counselor in Tampa, Florida.  My background is actually in finance. I worked in corporate America for almost 10 years.  I realized I was dying a slow death in my cubicle and I needed a drastic change. While I was still working, I enrolled in a graduate school program to get my Masters degree in mental health.  It was the best and hardest thing I’ve ever done for myself. Now I have my own private practice and love what I do every single day.     

If someone came to you for dating/relationship advice, what would they expect? 

Therapists are technically not supposed to “give advice.”  I work with my clients to identify the difference between healthy and unhealthy relationship components, and then we assess how they feel about their own situation.  I study a lot of modern day relationship experts (John and Julie Gottman, Esther Perel, Sue Johnson), and also draw a lot from my own experiences. One universal piece of advice is to stop comparing.  So many of us judge the health or happiness of our own relationships based on the milestones or timelines of others. We’re constantly trying to figure out what’s okay, or what’s normal. Not only do “okay” and “normal” not exist, their definitions vary from couple to couple.    

What are some of the projects you’re currently working on?

I am a huge advocate of adventure therapy.  My blog, which is definitely a work in progress, is geared towards helping people make that connection.  In many ways, travel and hiking have been the best therapists I’ve ever had. I want to help people understand that they can work on themselves and find healing and growth without sitting on a therapist’s couch once a week. We’re in the process of adding a travel section, as well as a map of hiking recommendations in different cities.   

Dating Dilemmas

Name: Anonymous

Age: 39

Gender: Female

“At what point do you know a relationship is over”

My answer to this question has changed over the years.  I used to think that a relationship would end if it experienced things like betrayal and trauma.  But over the years I have seen couples stay together, and sometimes come out stronger, after those events.  I currently believe that a relationship is over when at least one of you doesn’t want to keep trying.  

We have access to so many resources today.  There are so many books, videos, blogs, podcasts, and real life therapists to help us change, repair, and strengthen our relationships.  And they can work, if you are willing to take the time and make the effort. But if one person stops wanting to, that is a major indicator that you’re nearing the end.  

Two other possible indicators that your relationship is over are legitimate deal breakers or abuse.  Even the best therapy can’t fix one person desperately wanting to have a baby, while the other person adamantly does not.  And we know that abused women tend to stay and justify and hope for the best, but you could literally be risking your life by waiting.    

Name: Anonymous

Age: 31

Gender: Male

“I’m trying to work up the nerve to ask a girl out. Any tips?.”

Um… Just do it?  

Many people experience fear when faced with a situation that may result in rejection.  But when it comes to dating, that is the irrational thought that we need to change. If we ask someone out and they turn us down, we immediately go down a self-deprecating rabbit hole.  We start to mentally list all the reason’s we’re not good enough, and they feel so believable. Even though there are billions of people on the planet, it’s actually not that easy to find the person (or people – if you’re not in to soul mates) who is a good fit for you.  And it’s not because there is anything wrong with you. Or them. We get upset when we can’t fit the square peg into the round hole, and assume it’s because we are flawed in some way. There’s nothing wrong with peg or the hole, they’re just not a match for each other.

Other tips that might be helpful:  Decide what you want to say and how you want to say it before you are actually having the conversation with her.  If you’ve never talked to this person before, consider some other ice breakers to see if you’d even have enough to talk about during a date.  Have some ideas for where to go and what to do on the date, but it’s also a good idea to ask her if she has any preferences.        

Name: David

Age: 33

Gender: Male

“I’ve been with someone on and off for over a year now, things seem to go well for a little while then they just fizzle out. Is this something I should stick with or give up on? I’ve tried to ask myself this question and I’m stumped. Love some help.”

These relationships are sometimes the hardest to navigate.  We’ve identified that there is something about this person that we’re drawn to, but at the same time realized there is something that’s not working right.  

The question you need to ask yourself is, “Why do I feel this person is worth fighting for?”  Once we’ve done the back-and-forth a few times, we lose perspective because we fall into patterns of comfortability and familiarity.  It’s important to have a good grasp on your own personal values, goals, and what you want out of life. How else can you do an accurate assessment of whether or not your priorities align?  

I also noticed that you say in your inquiry that you’ve asked yourself this question.  If you haven’t asked your partner, that’s your next step.  You can get advice from a million people, but there is only one other person sharing in this experience with you.  We tend to be fearful of vulnerable conversations, but without complete honesty and transparency, you’ll continue to be in a place of uncertainty.  

Lola Vanderstrand

If someone came to you for dating/relationship advice, what should they expect?

I am a life and dating coach working with individuals and groups to identify barriers of personal challenges and my clients can expect me to deliver coaching and meditation solutions to improve their personal lives. The solutions are customised and personalised based on current needs and I give them a sense of motivation and confidence. 

What are some of the projects you’re currently working on?

I am creating personalised audio to facilitate change. Audio that encompasses affirmations, meditations, subliminal and other technologies for self-improvement.

Dating Dilemmas

Name: Anonymous

Age: 23

Gender: Male

“What advice do you have for a guy who’s too ugly and can’t find a date?”

Well, I don’t believe in “ugly” because beauty is in the eye of the beholder. Stop thinking of yourself as ugly and focus on the great qualities I know you have! There is a lid for every pot.

Name: Wayne

Age: 31

Gender: Male

“In Spring last year, my girlfriend and I went on a holiday together. On one of the nights of that holiday she spent a night not with me in the hotel, but somewhere else. She said she randomly met up with a friend who she bumped into – in a country on the other side of the world! It’s been a long time but I still have my suspicions. What should I do?”

Ask yourself what kind of relationship you want with your girlfriend, what is it you want for your future and know you deserve someone who is there for you. Communicate with her about how you feel and what your suspicions are. Do you trust her or is this coming from a place of fear?

Name: Anonymous

Age: 41

Gender: Female

“Got any helpful tips for a woman who has a crush on their assistant?”

Look for the signs that he is also interested and find out if he is already attached. Ask yourself if you want to work in the same work space in this time of workplace harassment. If you get attached, will the work still get done and what will happen if you break up? 

Samantha A. Gregory

Tell us about yourself

I am the author of, No More Crumbs: How to Stop Dating (and Mating) for Crumbs and Get the Cake You Deserve in 10 Crucial Steps. I am also a relationship recovery coach at NoMoreCrumbsDating.com who helps women recognize, reject, and release toxic people so they can recognize their worth, embrace their feminine power, and attract healthy love (and wealth).

If someone came to you for dating/relationship advice, what should they expect?

If someone came to me for dating or relationship advice, they can expect a listening ear, compassionate heart, and frequent reality checks. I believe in helping people face their truth and focus on becoming the best version of themselves.

What are some of the projects you’re currently working on?

I am working on the 2020 version of No More Crumbs, which will include learning how to navigate modern dating practices, more feminine empowerment advice, and interactive features that allow the reader to view related videos.

Dating Dilemmas

Name: Anonymous

Age: 25

Gender: Male

“Can a guy in his 20’s who’s also divorced find love? Because the answer so far has been no”

I believe anyone can find love despite past relationship issues/problems. The key is to first find love inside your own heart and fill every aspect of your life with love. Deal with issues from your past relationship and forgive you ex and yourself. Love sometimes feels elusive because you haven’t dealt with the painful divorce and are seeking a relationship to distract you from the healing work that needs to be done. 

Name: Anonymous

Age: 39

Gender: Female

“I’m on a streak of 7 bad dates, I’ve got my eighth in a couple of weeks. What can I do to make sure this doesn’t make it 8 bad dates? Is there anything I can do?”

A streak of bad dates is a clue that there is something going on with you. You are the common denominator in each scenario. Take time to review the dates and your behavior to pinpoint how you have possibly sabotaged your dates. If you are going in thinking it will be a bad date, you are getting what you are expecting. Try imagining this 8th date is the best you’ve ever been on and go with that good feeling. See how it goes. If it’s still bad, consider you may be choosing or agreeing to dates with incompatible people because you are not really ready to meet a good guy.

Greg Audino

Tell us about yourself:

As for your questions about me, I’m a certified life coach and in addition to my one-on-one clients (which I offer in person, over the phone, and even online coaching options for), I run a donation-based self-development website at gregaudino.com where I create funny, off-kilter videos that offer new perspectives of life’s common challenges.

My videos can also be found on YouTube and Patreon, and 10% of all proceeds I get are then donated to the World Wildlife Fund. For what it’s worth, I’m also an actor with principal roles on shows like Westworld, New Girl, NCIS, SWAT, Jane the Virgin, and more. My current project I’m working on is creating an online course, and after launching that I’m looking to expand into more speaking gigs, likely starting my own podcast, and something else way down the road that I can’t share quite yet! Should the users want to follow me on social media, Instagram is the best place and my account is @simplygreggles.

Dating Dilemmas

Name: Anonymous

Age: 35

Gender: Male

I suffer from a number of disabilities and dating can be quite hard. What do you recommend to help that?

Thanks for sending this question in! I’ve always felt as though dating with disabilities comes with a unique advantage; and that is that the relationships you do create (not just romantic) are much more likely to be based on substance rather than shallowness. Those who are unwilling to put the time in to get to know your struggle and your story are more likely to steer clear, thus leaving you with a network of people that genuinely care for you or want to try to. 

But when it comes to building those meaningful relationships, the same guidelines apply to those with and without disabilities. Here’s my line of thinking: 

Clarity About One’s Values + Living Through Those Values = Independence = The Right Connections 

Look, we all want to date. Reproduction and connection is deeply hardwired into each and every one of us. When that is deprived due to disability or anything else, the desire strengthens, and in turn, so does our codependency. When we have feelings of codependency, we start to engage in more and more behavior that is more aligned with what we think others want of us than it is with what we want of ourselves. These actions alienate us from good relationships, because we skip our needs in favor of the needs of others, thereby giving a false impression of who we are and attracting people who we aren’t fully compatible with. In this scenario, we become the villain because what we’re really doing is lying to people and using them for our own gain. 

To meet people we’re compatible with, we must meet like-minded people. To meet like-minded people we have no choice but to be living independently and doing things that have meaning to us outside of what others think. 

So first, get clear about what those things are. What means a lot to you regardless of what others think? 

Once you have that list, looks for ways to integrate those values into your day. Look for activities. If you like reading, go to more libraries and book clubs. If you like films, go to film screenings or Q & As. Perhaps you find a lot of value in causes that support and highlight the accomplishments of those who share your disabilities. Learn to make habits out of these things that you enjoy unconditionally, and do your best to replace them with activities you take part because you feel as though you should for the sake of attracting other people – which are easy to get in to as desperation and desire rises. 

The practice of these activities that are right for you is apt to bring you more independence, because you’ll be surrounded by the right communities who support you in an area of your life where you don’t even need support. You are now in partnership, and not being looked after. It’s these activities that bring you confidence and joy, further detaching you from whatever story you’ve made up as to why your disability is a prohibition. It’s within these communities that you can develop confidence and form the best relationships in all areas of life. 

A separate and final note I feel inclined to add is that, given your disabilities, I’m sure you’ve been through past trauma when people’s treatment of you. The need to defend oneself in a world without many others like you is a strong need. It’s a need that must be kept at bay, however. There are people in the world who want to love you, and in their process of learning about your struggle, miscommunication or misunderstanding may arise. Be patient with this as you want them to be with you. Talk through their concerns with them as you would want them to do to you. Relationships only work if we be the partner we want others to be, and that can be hard when we feel a particular need to look after ourselves.

Name: Mike

Age: 22

Gender: Male

How should I propose to my girlfriend?

This is hard to answer, as proposal is something to special and unique to each relationship. Some people love the rush of doing it in public with friends and family around, others find it too risky. Some people like the safety of being somewhere simple and alone, others like more flash. It goes without saying that you want to make a proposal memorable, for both your sakes. Look to her for the answers. Ask yourself how you can propose in such a way that’s both valuable and comfortable to her. Get into her head (not a blowjob reference) and try to consider what the ideal proposal would be, based on her interests and desires. You might even look to her friends and family for encouragement. This consideration of her needs is a perfect microcosm for the relationship going forward, so you might as well get the ball rolling now! 

That being said, there’s no need to feel pressured in this situation. Of course it’s an exciting moment, which is precisely why we don’t want it to feel like a chore. No need to obsess over getting it perfect – there’s no such thing. Oftentimes, missteps during the proposal make for a fantastic memory. Let this be an enjoyable milestone, as at the end of the day, the right woman will just be happy to be spending the rest of her life with you. 

Name: Paige

Age: 40

Gender: Female

I’ve just turned the big 4 0. How will dates and relationships change in my 40’s? How will it be different to my 30’s?

Good question! I think from the get-go, it’s important to realize that 40 is just a number. What 40 means to you is different from what it means to someone else. Thrusting opinions onto your relationships that mirror how you see 40 is a dangerous game, because we never want to be forcing anything or trying to uphold certain imagery in relationships. Up until this point, relationships have transitioned smoothly with age, haven’t they? Everyone is learning together, and it’s not like things suddenly change at specific ages. You’re probably much more prepared than you think, and these relationships will grow naturally, as do you and your partners. That in mind, let’s consider some general commonalities around this time: 

By 40, you’ve had plenty of life experience and come with plenty of baggage. You know this, and it’s important to be respectful of this should you choose to date someone who is your age. If you’re dating someone younger, it’s important that they respect this element of you. Unlike the younger years, more baggage means more conversations about real issues, more distractions in life (kids, work, etc.), and unfortunately, more moments of crisis. Though by 40 we are often established in who we are, those who feel unfilled with how they’ve spent their past are apt to acting out to make up for lost time (a la the mid-life crisis). Whether you find yourself or your partner doing this, patience is key, and exploring these feelings together is a great means of building relationships. 

On the upside, all of that baggage comes with a hell of a lot of knowledge, leading to better and more committed decision making. With a few exceptions, both you and any partner you take that is around 40 have clearer ideas about what you want, because you’ve learned first hand what you don’t want. You’ve also learned that madness that comes with all of the variety there is to choose from, thus making you more comfortable with commitment. Though commitment might mean different things for different people, aging is very much about minimizing (or choosing the fewer, better priorities), and minimizing means the confidence to commit to things without seeking everything better. It’s a wonderful thing, as I’m sure that when you look back, you’ll reflect on how much time you wasted on the many things you prioritized that proved themselves senseless in the long run. 

The most cautionary piece of advice I can offer, and where many people go wrong, is the necessity to give people a fair shot. As we age, we can feel hurried to start accomplishing that which we once set out to but haven’t yet. These expectations we put on ourselves, our lives, and therefore on those that allow into our lives, can kill a relationship at any age – but those chances increase as we get older. That being said, I’ll conclude my answer with an excerpt from a video I once created in which I answered a viewer question about wanting to let people in and wanting to have kids: 

“As time goes on, the desire to find that right person … can intensify in a big way, leaving many of us uninterested in people that may not show immediate signs of being “the one”, but you must remember that most long and happy relationships were not started by fairy tale moments. It takes time to know someone and get comfortable with them, and although we all know this in our heart of hearts, it’s easy to forget about it when you feel you’re running out of time. So ask yourself if you’re putting unfair expectations on dating prospects these days in a way that you didn’t when you felt you had more time. Of course it’s hard to let people in when your aim is to seek the right person for the rest of your life, rather than the casualness of allowing yourself time to get to know someone and not having such a strong negative reaction to whatever attributes they showcase that you don’t like. Forget about the clock, forget about the requirements. Allow people to have their faults just like you do, and you may find yourself more comfortable with letting people in.” 

Rosalind Sedacca

Meet Rosalind Sedacca, CLC

I am a Dating In Midlife Expert and Dating & Relationship Coach as well as the co-author of 99 Things Women Wish They Knew Before Dating After 40, 50 & Yes, 60!In addition to coaching clients via Internet and phone, I also facilitate workshops, webinars and teleseminars on dating and relationships for single women and men. For many years I’ve been blogging and writing expert articles for the Huffington Post, Bustle, Chic Galleria and numerous other websites and blogs on relationship issues. I host the Divorce, Dating & Empowered Living Radio Show and Podcast on the Going Solo Network, iHeart Radio and other venues. In addition I am co-creator of several online programs and courses for singles that can be found at: womendatingafter40.comwomendatingrescue.com and mensdatingformula.com. Contact me directly at [email protected].

If someone came to you for dating/relationship advice, what should they expect?

Caring, compassionate support and immediately usable suggestions about how to approach their challenges in a new and different way. My clients don’t get stuck in victim roles. They discover how to make different choices to get different and better results. They explore ways to forgive themselves for past mistakes and attract the love partner who complements their needs and lifestyle. My approach is spirited, interactive, supportive and encouraging every step of the way. See the client praise found at womendatingafter40.comwomendatingrescue.com and mensdatingformula.com.

What are some of the projects you’re currently working on?

I’m soon launching an online Co-Parenting Club for singles with children. I am being interviewed on several new podcasts and scheduling new interviewees for my own radio show, Divorce, Dating & Empowered Living With Rosalind Sedacca. I’ve recently updated my popular Women Dating Rescue 10-week e-Course with new resources and content.

Dating Dilemmas

Name: Sarah

Age: 49

Gender: Female

“I’m now divorced for the third time. I’m set on not going through the hassle of ditching another husband again, I really want to enjoy myself. Where does someone my age start?”

You start with a sincere deep desire to learn why you’ve chosen the partners you have had and what you’re going to do differently moving forward. Otherwsie you’re destined to repeat the past leaving you frustrated, angry, hurt or bored. Only when you decide to use fresh criteria for selecting partenrs will you have a chance to meet interesting, caring and quality people who are worth your time and energy. Don’t waste more of your life choosing the same old guys with different names and faces. Understand who will be a worthwhile love partner and change your ways!

Name: Anonymous

Age: 41

Gender: Female

“I haven’t had much luck finding a guy my own age and have started dating guys younger than me. Nothing too crazy, 5-10 years younger. Is what I’m doing right? Am I just setting myself up for heartbreak?”

Age is not the most important criteria when choosing relationship partners. Younger men can be stimulating, invigorating and fun to spend time with. Even to settle with. There’s no right or wrong about this. What does matter is whether they respect you, treat you well, honor who you are at this age and want to continue being with you. Heartbreak comes from unrealistic expectations and not knowing who you are choosing. So get to know your partner to see if they are with you for the right reasons, or just for short-term fun!

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