'What signs of mutual interest or comfort should someone realistically look for?'

"I don't want to escalate too quickly and create pressure."

Dear Dollar Signs,

I'm a 21-year-old navigating dating after a meaningful past relationship and I'm struggling. How do you know when it's actually the right time to ask for someone's Instagram or ask them out? I don't want to escalate too quickly and create pressure, but I also don't want to miss opportunities by hesitating too long. What signs of mutual interest or comfort should someone realistically look for before taking that step?

I'd appreciate guidance on balancing emotional maturity, timing and confidence - especially in your early 20s when your finances and identity still feel like works in progress.

Still Single

If you're just starting out on your money or career journey and have questions about how to navigate your finances, we want to hear from you. Write to Dollar Signs, MarketWatch's new advice column, at dollarsigns@marketwatch.com.

Dear Single,

You are not going to like this answer, but I do wish someone had plainly explained this reality to me when I was younger: There is no way to date without risk or rejection.

Unless you are one of the elite, effervescent few who have never experienced unrequited interest, dating requires a certain level of bravery.

"People want to have so much assurance that the other person is going to say yes before they do anything," says Grace Lee, a New York City-based dating coach and matchmaker.

'People are running around the world handing a report card to people who shouldn't have that power.'Sabrina Romanoff, clinical psychologist

"Taking risks - that's the vulnerability element of dating that you need to get comfortable with. If you are looking for 10 signs that this person will say yes, you probably will miss the opportunity waiting for that 10th sign," Lee says.

Your ego might take a hit. Your wallet might, as well. Dating is expensive, and you're not the only one feeling this way. Among Generation Z and millennial singles, 40% are choosing to go on less expensive dates, according to data from Zelle. Meanwhile, 52% of Gen Z daters have ghosted, blocked or unfollowed someone at least once to avoid paying them back after a date.

There is no way to totally protect your self-esteem or your bank account, but you can make smarter choices about who you ask out by taking some preliminary steps before a date.

Ask questions

The best way to gauge if someone is interested in dating is to see how they respond to a text that isn't asking them out, Lee says.

"Send an innocuous text, and if they are interested, they will respond and put a bit of effort into the response," she says.

I always say that dating is not all that dissimilar from making friends. If you texted an acquaintance you wanted to know better and they gave you one-word responses and never asked you any questions, it would be pretty clear that they weren't interested in pursuing a deeper connection. The same goes for dating.

Text the person. Ask a thoughtful question. If they send a detailed answer and respond with their own questions, and if you two develop a good rapport, there is a good chance they want to get to know you better and would be willing to go on a date.

Pick affordable dates

A date doesn't have to be pricey to be good. Getting asked out to an affordable happy hour where beers are $5 might actually be a bigger green flag for someone than a date at a fancy cocktail bar.

In fact, 38% of singles judge someone positively for planning an affordable, thoughtful date, according to data from Zelle. Only 23% of daters said the same of extravagant, high-end dates.

The point of the date is to get to know the person better, not to attempt to impress them with how much you can afford to spend.

Don't add them on Instagram

When it comes to Instagram, Lee says it's best to not add potential dates at all.

"It creates another layer of confusion," she says, "if you look at their story and they don't look at yours, things like that. None of that makes it easier. What it does is it just creates another layer you need to go through to see if someone wants to go out with you."

It can also deter you from, or attract you to, a person who doesn't exist. We all know that social-media personas can be misleading. If you add someone on Instagram before actually getting to know them, you might get attached to a representation of their life that isn't accurate.

One of my friends is in a five-year relationship and met her partner at a bar. She didn't follow him on Instagram until they had been dating for a few months, and she often tells me that if she'd seen some of his photos early in the courtship - the one he posted of his PlayStation high score, for example - she isn't sure she would have gone out with him. Today, they are happily living together. Clearly, judging him by his Instagram would have been a mistake.

Do yourself a favor and eliminate social media from the equation.

Reframe rejection

We sometimes prioritize the opinions of those we are dating before we really know them, says Sabrina Romanoff, a clinical psychologist who specializes in dating.

"People are running around the world handing a report card to people who shouldn't have that power," she says. "It's a completely illogical experience, and we do it because we are not so sure of ourselves."

Take stock of all the people in your life who already love you and see you. Count your wins and celebrate who you are outside of the romantic context.

Remember, the most important part of dating is you. You cannot control whether someone likes you, but you can reframe what rejection means.

Relationship therapist Lisa Marie Bobby always says to "fail as fast as possible."

"The goal of dating is to meet people and discover if there are mutual points of compatibility and fun," she says. "Is this a fit? The faster you can get to know someone, the better, so that any time someone doesn't want to date you or you decide you don't want to date them, that is something to be celebrated."

You don't want to waste time, money or energy on someone who is not a potential long-term partner. So whether they end it with you or vice versa, that's an outcome that you should actually strive for if the person isn't a good fit.

If you are thoughtful about who you ask out and do a bit of screening beforehand, you're more likely to meet people who might align with what you're looking for in a partner, and less likely to spend money or time on those who don't.