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30 Dating Dilemmas in 30 Days – Angela J. Thompson

Your favourite UK cougar 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

My name is Angela J. Thompson.  I am an Executive of multiple enterprises and a seasoned Business, Life and Success Coach.  I have achieved various levels of success personally and pride myself in being a resource, through which others are able to reach the levels they seek.  Specifically, in the dating/relationship space, I have developed an online tool for singles who seek long-term relationships and/or marriage, 

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

In the event that someone approaches me for dating/relationship advice, they could expect that I would assess their personal thought and attitude about dating.  Upon understanding their personal approach, I begin to evaluate their feelings because emotions are the direct link to their motivation. 

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

I am continually generating content for our Marriage Minded Only blog and contributing to dating/relationship publications.  I am also making appearances at dating/relationship conferences and interviewing with various interested media sources. 

I am also a contributing author to the anthology, The Diary of A Ready Woman, sold on Amazon. 

Dating Dilemmas

Name: Anonymous

Age: 55

Gender: Female

“I’m dating someone 15 years younger than me. I’m so happy and have never enjoyed a relationship this much. But I don’t know how to tell my family and friends. What should I do? How should I go about telling them?”


Dear Anonymous, 

Dating a younger individual can be exciting!  It can give you a certain level of validation and can be freeing!  You get to be you, while feeling valued and alive!… On the other hand, you can also feel judged by others who are not experiencing your newfound freedom and validity.  The best approach to sharing your excitement and joy of dating this person with family and friends is to be solid in the benefits of being in the relationship. When you are grounded in, i.e., “how he/she makes me feel,” “he/she supports my dreams,” “he/she wants to build with me,” it is really good news to share and you should not feel ashamed, nor afraid because this person is positively contributing to your happiness and well-being.  Which is absolutely what all of us want, right? When you are firm in understanding and benefiting from their contribution to your life, you can firmly and confidently say, “I am dating him/her” and really feel good about your decision, therefore maintain your stance with all others. 


Angela J. Thompson

Name: Steven

Age: 30

Gender: Male

“Do women appreciate being asked out randomly in public? Can I ask someone for their number in the street or would I always be seen as a creep?”


Dear Steven: 

Dating in this virtual world of texting, DM-ing, Inboxing and Snapchatting, the act of approaching an attractive and interesting person may seem archaic and creepy, but it is the most practical way of making your appeal.  Stepping out of the “now” norm and asserting yourself is an act of bravery and heroism. Especially, if you walk away with the win! Though it can be intimidating and feel like a violation, according to today’s standard, it can build character, earn you respect and set you apart from many others.  So, if you see someone you really would like to get to know, conquer your fears and approach them respectfully. 

Greatest of Luck to you!

Angela J. Thompson

Name: David

Age: 27

Gender: Male

“Why has my girlfriend gone off sex? I care about her but this lack of intimacy is killing me. It’s been close to eleven months. Am I a jackass for being upset?”


Dear David, 

Sex is very intimate.  As women, we engage when we want to get closer or remain connected.  It is not always deemed a “need” for a woman, but oftentimes a desire. So,  when a woman chooses to engage in sexual contact, within a committed relationship, desire has to be present. 

By no means are you wrong for being upset.  This issue is more personal for you because, sex is typically a necessity for men.  It’s very natural to be upset, but you have to go against your nature, sometimes, for the woman you love to get to the root of the problem. 

You can toss around a lot of questions and feelings, during a stressful time like this, but you have to genuinely connect to her feelings to understand the underlying issue.  Is she depressed? Is she angry with you? Is she worried about something? You must ask the necessary questions, assuring her that you really care. Then help her seek the proper assistance if the matter is beyond your control and/or level of expertise. 

Hoping for the best, 

Angela J. Thompson

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