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30 Dating Dilemmas in 30 Days – Greg Audino

Your favourite cougar dating site, Toyboy Warehouse has 30 days to gather the most influential dating and relationship experts to help answer 30 dating dilemmas from real members. It’s a race against time to solve the world’s love issues, will we make it?

About you

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.” 

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