Where to Take a Single Mom On a Date

Dating is nothing like it was five years ago, and for good reason. Many of us have evolved past what our parents and grandparents believed traditional courting should look like. That may have involved a man arriving at a woman’s house, asking her parents' permission to take her to a movie or a diner, and maybe even for a walk. Nowadays, with so many of us experiencing different people at various stages in our lives, it may come as no surprise that we’ve had to pivot.

Women in the early ’90s, and even as far back as the ’70s, did not have the options women do today—the option to stay single and provide for themselves. Nowadays, this is no longer seen as taboo, which leaves many men needing to keep up with the times and get creative when it comes to courting a woman who is either a high-income earner, a single mother, or a recently divorced woman. All of these women will have different standards for the men who wish to come into their lives, and here, I’m going to break it all down for you to better understand.

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HIGH-INCOME EARNERS are women who earn anywhere from $78,000 to $150,000 a year, whether through content creation or working a traditional corporate role. She’s not going to be interested in dating a man who is not either on her level or higher—granted, some men will look to demonize these kinds of women depending on their profession. If she’s an OF model earning the aforementioned salary, then for some men, this is not something to respect. However, if she’s a forensic psychologist, then it’s different, and he will be more likely to respect her boundaries and standards for a relationship.

Dating this type of woman requires a strategy. You need to leave your pride at the door and understand that her career is most likely going to be the central focus of her life because there’s a significant reward she is trading her time for. As a man, if you’re looking to get this woman’s attention, you will need to convince her that spending time with you will net her a positive reward.

That could be a wonderful date filled with unforgettable memories or a conversation over the phone that intrigues her mind and makes her excited to get to know you. Either way, your first priority should be understanding that her time is valuable—her job thinks so, and so does she. She knows her value, so you need to enter this dynamic with the same understanding and put forth maximum effort to get this woman to put you on her radar.

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Some date night ideas? This article is all about thinking outside the box while still being mindful of your privilege as a man. Ask her about her hobbies—since she’s a career woman, she’s probably eager to do something that allows her to let her hair down and have some fun. Send a car to pick her up and consider taking her to an indoor trampoline park. Another option could be a helicopter ride around the city, indoor skydiving, followed by a nice meal. To spruce things up, you can also suggest a shopping trip, proposing a budget early on of around $400.

SINGLE MOMS are not hard to date, despite what others say online. While there are a number of stories of single moms either taking their children with them on a first date or trying to swindle their date into paying for extra food to take home for their kids, these women are few and far between. The likelihood of experiencing this type of behavior is low as long as you keep your standards high. But let’s say you do meet a lovely single mom who is open to dating you.

Think of something nice to do that allows you to get to know one another while still benefiting from your time together. This could be attending a horse racing event where you bet on horses, going for a midday stroll in a park, or my personal favorite—a trip to the casino. Hear me out! I remember a man asking me on a date, and I was very excited when I learned we would be going to the casino. Not only because it was unconventional, but also because he gave me money to bet with and told me I could keep my winnings.

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He bought us drinks, we talked the night away, and it was a chance for me to gain more information about who he was while also earning some money. If you’re trying to test the waters to see if your single mom date would be interested in this kind of outing, consider bringing up an online casino casually during your conversation. If she’s open-minded, then before the date, you can propose a game. Some online casinos offer no wager bonuses, so you wouldn’t be losing anything if she’s bad at placing bets or just shows little to no interest in it altogether.

For the average single mom, she’s not looking for a man with a gambling problem—no. But she is looking for a man who is resourceful. Being resourceful means you can earn money for your family and put her in a position to earn income as well. Either way, this is a great way to see the kind of woman you’re dealing with and decide whether or not to continue the relationship.

Last, we have the recently DIVORCED WOMAN , who will no doubt be comparing her new suitor to her past lover. If her ex died prematurely, then depending on when this occurred, it’s probably best to give her some space to heal. On the other hand, if she’s divorced due to her past lover cheating on her, etc., then you want to do an activity that will help her heal, allow you to learn more about her, and provide an opportunity for you both to enjoy one another’s company with few distractions.

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Some great options include the spa, which is excellent for a first date. Divorced women often tend to stop pampering themselves depending on the nature of their breakup. If she’s going through a slump, then a spa date will lift her mood and show her that you’re willing to not only invest in getting to know her but also ensure that she feels her very best at all times. Another option to consider is golfing or attending a baseball game. Both of these activities are calm enough that you can ask each other questions but lively enough that you can both enjoy the experience as a new couple.

There you have it! If you decide to try out any of these, shoot us an email and let us know.

by Danielle Wright