Overcoming Self-Doubt with My Sugar Baby’s Support

If you had asked me six months ago if I was an insecure person, I would have told you that I didn’t have time for that kind of weak, self-pitying mindset. Only, I probably would have used a lot more expletives in my response.

That’s because, at the time, I had an idea of insecurity as something that “weak” men had. I had a vision of these guys as nerdy, soft, fantasy game-playing weirdos who never talked to women and had never seen the inside of a gym.

I was, and am, the opposite of that. I have a well-paying job in finance. I dress well. I go out with my guys, and we hit on women, and it works. I do CrossFit. I eat a high-protein diet.

It took me getting to know Red to realize that, despite all of that, I was actually dealing with some deep-seated insecurity, and it was robbing me of my happiness.

Red is a nickname, of course. But it’s how she introduced herself to me when we started chatting online on a sugar dating website. I asked her if it was because she had red hair, and she said, “That’s a good guess, but it’s actually because red was my favorite color growing up, and my teachers and my friends started calling me red because of how much I wore it.”

“Doesn’t that seem like they were making fun of you a little bit?” I asked.

Red seemed surprised at that take. She said, “No, it was all in good fun. Why was it something that kids would have bullied each other about at your school?”

“Absolutely,” I responded. “We could be relentless as kids. One time, a kid came to school with a tiny stain on his shirt, and we called him Spaghetti until high school. I think he was so embarrassed, he never dared eat spaghetti when it was being served in the cafeteria.”

“That’s awful,” she responded, and then logged off for the night.

I was confused. I had meant that as a funny anecdote, but Red had taken it the wrong way. I chalked it up to her being overly sensitive and decided that maybe we weren’t going to be a good match after all.

But the next day, Red reached out again and asked if I would want to meet up.

“I feel like it’s hard to read you over messaging,” she said. “Would you want to go out for ice cream?”

As I said, I’m a pretty health-conscious guy, so this didn’t appeal to me. I told her as much.

“Oh, don’t tell me you’re too insecure to have a little ice cream with me!” she said with a winking emoji.

I resented this, but I decided that she was right. We maybe just weren’t understanding each other over messaging. I told her as long as the place had some dairy-free options, I was in. She sent the rolling eye emoji and then a smiley face. We agreed on a place and set a date.

Red was gorgeous in person (with blonde hair, in the end), but I was dismayed to find that I was only about an inch taller than her. If she stood up really straight, or wore heels, we would be the same height, or she would be taller. I’ll admit that this was a red flag for me. I felt like everyone was looking at us.

I bit my lip, though, so that we could get through our ice cream date without too much awkwardness.

The date itself got off to a pretty good start. Red was charming and relaxed. She put me at ease. She asked about my gym routine, since it seemed like a big interest of mine (she playfully squeezed my bicep as she did so, which gave her extra points in my book), and she told me that she also liked to work out, but more for the enjoyment and the mental health benefits. She dealt with anxiety sometimes, and a strength workout was always her quick fix. This seemed overly vulnerable to share on a first date, but I let it go.

After about an hour of chatting and walking down the pier with our ice creams, I nudged Red’s arm playfully and said, “So, now you can see I’m not insecure. I went for the cookies & cream.”

Red rolled her eyes, equally as flirtatious, and said, “I’m still not so convinced.”

This wasn’t the reaction I was expecting, and honestly, I felt a flash of anger.

“What do you mean?” I asked.

“Oh, well, you seem like a nice guy, don’t get me wrong. But I’ve had sugar daddies who are ‘gym bros’ before, and usually, once we’ve been dating for a while, they tell me about how they really feel about themselves. How much they feel like they need to have the perfect body or have a lot of money to prove to the world that they’re worth something. They have this constant negative self-talk going on that I can imagine is really tough to live with. I’m not saying that you’re the same way, by any means. I’m just saying that I would need to get to know you a little more.”

I stayed quiet, and I think Red realized that she had soured the mood.

“Hey,” she said, trying to lighten things up again. “Aren’t we all a little bit insecure, deep down? I know I am.”

“I guess I don’t really think about it the same way that you do,” I said, maybe curtly. We changed the conversation.

Back at home, I did start to think about what Red said. Maybe I was living from a mindset of having to prove myself, of having to compete. Without a doubt, the world of finance rewards the competitive. And I had been competitive enough to get ahead.

But how many times had I looked at myself in the mirror before work, thinking, “They’re going to fire you today?”

Or, how many times had I gone to the gym and been embarrassed to stand next to some guy who was way more buff than me? How many times had I broken up with a girl because she was almost taller than me? Because I thought it would make me look bad around other guys?

But more than all of that, the thing that Red said that really got to me was the negative self-talk part. I realized that the voice inside my head was what had gotten me to a place of success in my career and in my fitness goals. But even I had to admit that that voice was exhausting sometimes.

Maybe it seems obvious to the people reading this, but I had never put two and two together in terms of insecurity and self-criticism. Once I did, I realized that I was quite insecure. Maybe overwhelmingly so. I didn’t have a particularly positive self-image. I was constantly insulting myself. Constantly comparing myself to others.

I tried texting Red about it, but she quickly let me know that she would rather have this kind of conversation in person. So, we set up another date. This one would be our first real sugar date, so we picked a nice place. I hoped that Red wouldn’t wear heels.

Of course, Red did wear heels. And she looked insanely gorgeous. I looked like a potato next to her.

“Did you have to wear heels?” I asked her, trying to control my burgeoning bad mood.

“I thought you wanted to talk about insecurity? So I thought it might be a good ice breaker. Plus, they’re new!”

Her light-heartedness made me feel even worse.

She grabbed my knee under the table and said, “No, but hey. I’m really glad you reached out. And I want you to know that you’re in good hands with me, you know, to talk about this kind of stuff. I know how it feels to be hard on yourself and to think that that’s a normal way to live. But it’s not the only way to live. Look at you: you’re successful, you’re on a date with a beautiful younger woman, you’re in great shape. But you still feel like that’s not enough. It’s tiring, I know, constantly thinking that you don’t deserve what you have or that you have to prove to everyone else that you’re good and cool. With me, you can just be here. Just be yourself. Stop thinking about everyone else. Let’s just be here together.”

Obviously, Red didn’t cure my self-doubt with just one pep-talk. But I did feel something open up inside of me as she spoke. And I felt like I could stop looking around and just focus on the two of us.

Six months later, Red doesn’t have to interrupt me quite so often to say things like, “That wasn’t very kind to yourself,” or “Will you stop assuming that everyone’s judging you? You’re fine.” And I don’t have to interrupt myself quite so much, either. And that’s not to say that my life has changed all that much. I still show up to work the same way. I still work out and watch what I eat. But I’m able to enjoy what I have a whole lot more than before.

And I have Red to thank for that.