This is going to be my second Valentine's day as a single person, having previously had a girlfriend for almost 7 years. My last relationship was also my first relationship, and so in some sense, I'm a newbie to the dating scene, just like how many of my peers are new to investing.

My first thought when I got into the dating game again was to outsource the work, and hope for the best.

The hands-off approach

I asked my female friends if they knew any single women. Seemed easy enough. Your friends generally know you the best, and they'd probably be able to source the type of woman I'd like based on my own personal attributes and preferences.

Failure and thoughts

The approach above didn't really work. I didn't take personal responsibility, and I wasn't sure about what my objectives were. I wasn't able to get my friends to help me when I couldn't specify the type of girls I liked. I realised that my fantasies and failures are similar to what my friends go through when they start to look at investing their money.

Love and investments - drawing parallels

I often hear my friends making comments like these:

"Hey, I don't want to do the investments myself, you seem like you know what you are doing. Look, I'll even pay you to do it."

"My financial advisor told me I need to put in $1,500 a month, in a Investment Linked Policy, locked up over 20 years and I would be able to retire well, have I done the right thing?"

"The market should tank really hard due to the Virus! I will wait for the 20% drop in the market that I have waited so long for and I will go all in!!"

The denial of personal accountability and failure

While I want to give them credit for thinking about their finances, just like how I wanted to pat my own back for thinking about dating again, I know that isn't enough. Here are some things we've done wrong:

1. Avoided taking as much personal accountability as possible,
2. Not knowing what we want, and just committing to something because someone or some products make themselves available for us, and
3. Playing into our own false hopes.

Embracing vulnerability and self-love

To succeed, we have to accept that failures, disappointment and losses are part of the journey. It is the same in love as well as for investing. In love, we have to accept that we may be awkward, or get ghosted. In investing, we have to embrace that short term losses are a given when the market goes through a downturn or a correction. Letting ourselves be vulnerable, knowing when to step back and not trying to control outcomes are what we could do for both of these scenarios.

As Brene Brown, the internationally-bestselling author of Daring Greatly, says, "The truth is that falling hurts. The dare is to keep being brave and feel your way back up." To keep on trying in the dating scene despite the failures, and to remain invested when the market falls, are both big takeaways.

Be it our love life or our investments, let's celebrate our vulnerability and learn self-love and responsibility this Valentine's Day.