Is It Worth It To Shoot Your Shot? Here’s What 4 Dating Experts Suggest


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Dating these days can be challenging. From dealing with dating apps to getting ghosted, many women become disillusioned with dating and decide to give up altogether. However, some choose to take their romantic relationships into their own hands. Damona Hoffman, a relationship coach, always encourages her clients to empower themselves by getting out and trying to date. “For over a decade, I’ve coached women to be the chooser rather than sitting around and waiting to get “chosen,” but with the proliferation of dating apps, this has never been more true. Women who are bold about shooting their shot are much more likely to find the relationship they want online or offline,” she says to ESSENCE.

According to a recent study from Social Discovery Group, 77% of female daters over 45 are initiating contact, and women are twice as likely to get a response than men if they send their first message online. Hoffman has an easy but effective solution for those with difficulty navigating the new dating landscape, including apps. “My easy formula for shooting your shot on a dating app is “Comment + Question.” You should comment on something that stands out to you in their profile and then ask one question that requires more than a yes/no response to engage them in conversation,” she states.

Hoffman continues, “ The biggest mistake I see women making on dating app messages is sending too much in that initial exchange, which leaves the other person overwhelmed and unsure of what to react to. Make it easy to get into a volley with you quickly and let the details unfold over time.”

She also suggests that women shoot their shot but be completely unattached to the outcome, as she believes that’s what men have been doing for years. “Also, remember it’s not a rejection of you because they don’t even know you yet. We don’t know what that person’s history is, what their relationship status is, what they are looking for, or anything else about them when we shoot our shot, so we can’t get attached to the fairy tale at that point because we’re missing so much of the story,” Hoffman says.

Hoffman believes that being bold in communicating with a future partner will yield more positive results than not. “In real life, I encourage my clients to be bold when they have an interest in someone. A simple statement like “You should take my number” or “Let’s talk about that over drinks” can cue the shift from a casual conversation into a flirtatious one. If you bring the heat, you’ll see quickly how the other person reacts. If you keep playing it cool, you might get yourself stuck in the friendzone instead,” she says. 

However, it’s important to note that there is a big difference between shooting your shot and chasing someone. When someone is being chased, their initial instinct is to run. A relationship has to be reciprocal, so if you shoot your shot and get shot down, you have to be willing to hear the no and move on to conserve your energy for the next yes.

The mechanics of shooting your shot, according to relationship coach Beverley Andre:

What are the benefits of shooting your shot? Any downsides? Shooting your shot can be incredibly empowering as a person takes initiative in love. This is a great opportunity to boost confidence and bypass the dating games as you move with clarity. It also allows people to confront their fear of rejection, which can cause an emotional hindrance. When you put yourself out there, you’re actively seeking connection and increasing the likelihood of intimacy. However, the downside of shooting your shot is the possibility of rejection, which can lead to disappointment or decreased self-esteem.

How often should you do it? Shoot your shot as often as you want to create the opportunity. It’s less about a specific frequency and more about emotional intelligence and reading the room. Take the initiative when the moment feels right—whether expressing your feelings, pursuing someone you’re interested in, or advocating for your needs within a relationship. While there are no set rules, regularly step up in moments that align with your genuine desires while respecting boundaries and allowing space for reciprocity.

How should you handle rejection? While rejection is not for the faint of heart, it presents an opportunity to practice growth and resiliency, especially concerning personal wellness. Rejection is not a reflection of your worth. Someone saying no or not being interested can be due to misaligned timing, readiness, or compatibility. It’s ok to feel disappointed, but be mindful that you don’t allow that to define who you are and what you believe about yourself.

Share several ways to shoot your shot on dating apps in real life. Being online can be impersonal, so when shooting your shot on a dating app, give more than a simple hey/hi. Look through their profile and see what mutual interests you have to spark a conversation from there or kick off the conversation with a compliment about their interests instead of compliments solely around physical attributes. Asking an open-ended question can also help with building a connection. When shooting your shot in person, you want to take advantage of making your presence known. Make eye contact and smile. Be mindful of how you’re presenting yourself. You can even go as far as letting the person know how you came about shooting your show (i.e., I saw you come in and wanted to introduce myself.) Keep things light, but maintain confidence in your presence and communication.

According to matchmaker Tennesha Wood of The Broom List and dating coach Monique Kelley, shooting your shot doesn’t require a grand gesture. Small, low-risk moves can be just as effective. Here are some easy ways to get started:

  1. Ask a Question: Approach in a casual, non-romantic way. Say something like, “You ordered the lamb—how is it? I’m thinking about trying it.” If he’s interested, he’ll keep the conversation going and take the lead from there.
  2. Pay a Compliment: A simple comment like, “I love that shirt; the bold color suits you,” can open the door to further conversation. If he’s intrigued, he’ll engage and move things forward.
  3. Use Eye Contact and a Smile: Sometimes, a glance and a smile can do more than words. If he’s interested, he’ll make an effort to continue connecting.
  4. Notice Details: Commenting on something specific, like a watch or a book he’s reading, can spark genuine interaction. A man who is drawn in will extend the moment.
  5. Ask for a Favor: Something as simple as “Could you watch my bag while I run to the restroom?” or “Can you help me grab something from the top shelf?” creates an opportunity for connection.
  6. Be approachable: Smiling and striking up a conversation while out and about is always a great way for women to shoot their shots. Flirting is an art form that has taken a back seat due to the rise of dating apps. However, many singles are suffering from dating app fatigue. So, they are going back to organic ways of meeting people. When out and about, shoot your shot with the power of your smile and great conversation.
  7. Leverage homecoming season: HBCU Homecoming season is about to be here! This is the perfect time to shoot your shot with your college crush (who is single and divorced). Let them know you always had a crush on them, even back in college, and see how it goes from there.
  8. Lean on your friends: Let friends know you’d like to be set up with a single friend. Let them know one of the friends has caught your eye. Remember that some friends will say, “I don’t know about him, I’ve heard this and that… or my husband said this or that about him.” Just because he was one way with one person doesn’t mean it will be the same situation for you. So tell them to make the connection, and you can decide the deal.
  9. Workout: This is the best way to shoot your shot. Whether you’re at the gym, in a running club, or in the same yoga classes, you can start to build rapport while letting them know you’re interested. Ask them to spot you when lifting heavy weights, run with you during the running club, help you perfect a yoga pose, etc.

No matter how you approach, if a man is truly interested, he will keep the conversation going. And even if the shot doesn’t land, you’ll never have to wonder what could’ve been. The confidence you build by putting yourself out there is a win. Being vulnerable this way can feel risky, but love is always worth the risk.





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