Get the latest from the blog:

30 Dating Dilemmas in 30 Days – Brianne McGuire

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?

Tell us about yourself 

I research and document real sex for the purpose of inspiring people to accept every part of themselves. I am the host / producer of the podcast SEX COMMUNICATION and founder of GRAPHICPAINT, both of which feature honest, explicit accounts of life and sex. 

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

My advice is well-informed, bullshit- and judgment-free, and slightly humorous. Ask me anything but be prepared for some hard truths! 

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

Right now I’m working on the next phase of development for my platform GRAPHICPAINT: building out a sex-positive, media-sharing community with a new site and custom app. I’m also working on the production of original explicit content in collaboration with other sex-positive volunteers and media-makers. 

Dating Dilemmas 

Name: Anonymous

Age: 45

Gender: Female 

“I’ve only recently come out of a very long marriage and haven’t been with another man for almost 25 years. I’m so nervous about an upcoming third date. What should I do?” 

MASTURBATE. Reestablish connection with your body, desires and fantasies; approach this upcoming date as an expert on your own sexual satisfaction. Having this confidence and knowledge of self will put you at ease, and allow you to embrace the encounter as an opportunity for pleasure. 

Name: Anonymous

Age: 40

Gender: Female 

“I hate to have the most cliche, dating question but… how do I know if a guy likes me? There’s a guy at work, we’ve flirted, been friendly with each other but he hasn’t made a move.” 

Your gut knows what’s up and if you suspect he likes you, then he probably does. But more importantly, do you want to be with someone who isn’t willing to make the first move? This isn’t a statement on gender roles, but about knowing what characteristics are important to you in a partner. If you are comfortable being the dominant in a relationship, ask him out; if you are more at ease being pursued, find someone else. 

Name: Anonymous

Age: 33

Gender: Male 

“What’s a surefire way to spice things up in the bedroom?” 

SHOW your partner what you want — share the porn you watch, masturbate in front of them, introduce a device you’ve fantasized about using, etc. When you share these specifics, you are demonstrating trust, confidence, and exactly what you need to get off. Your sexy show is not only an education, it’s the opening of a door to increased communication and experimentation. 

Get the latest from the blog: