Is It Worth the Shot? Here’s What 4 Dating Experts Suggest

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Dating these days can be a challenge. From dealing with dating apps to being ignored, many women get disillusioned with dating and decide to give up altogether. However, some decide to take their romantic relationships into their own hands. Damona Hoffman, a relationship coach, always encourages her clients to empower themselves by going out and trying dates. “For over a decade, I’ve been teaching women to make their own choices instead of sitting around and waiting to be ‘chosen,’ but with the proliferation of dating apps, that’s never been more true. Women who are brave enough to try have a much better chance of finding the relationship they want, online or offline,” she tells ESSENCE.

According to a recent study by Social Discovery Group, 77% of women over 45 reach out, and women are twice as likely to get a response than men if they send their first message online. Hoffman has a simple but effective solution for those struggling to navigate the new dating landscape, including apps. “My simple formula for taking a picture on a dating app is ‘Comment + Question.’ You should comment on something that stands out on their profile, then ask one question that requires more than a yes/no answer to engage them in conversation,” she says.

Hoffman continues, “The biggest mistake I see women make in messaging on dating apps is sending too many messages in the initial exchange, which leaves the other person overwhelmed and unsure how to respond. Make it easy to get into the exchange quickly and let the details unfold over time.”

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

Hoffman believes that being bold in your communication with a prospective partner will yield more positive than negative results. “In real life, I encourage my clients to be bold when they’re interested in someone. A simple statement like, ‘You should get my number,’ or, ‘Let’s talk about this over drinks,’ can take a conversation from casual to flirty. If you bring the heat, you’ll quickly see how the other person reacts. If you stay calm, you could end up stuck in the friendzone instead,” she says.

It is important to note, however, that there is a big difference between taking a shot and chasing someone. When someone is being chased, their first instinct is to run away. The relationship has to be mutual, so if you take a shot and get shot down, you have to be willing to hear a “no” and move on so you can conserve your energy for the next “yes.”

Shot Mechanics According to Relationship Coach Beverley Andre:

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

How often should this be done? Shoot as often as you like to create an opportunity. It’s less about frequency and more about emotional intelligence and reading your surroundings. Take the initiative when the time is right—whether it’s expressing your feelings, pursuing someone you’re interested in, or advocating for your needs in a relationship. While there are no set rules, regularly step in at times that align with your true desires while respecting boundaries and leaving room for reciprocity.

How to deal with rejection? While rejection is not for the faint of heart, it is an opportunity to practice growth and resilience, especially in relation to your personal well-being. Rejection is not a reflection of your worth. Someone saying “no” or not being interested may be due to timing, readiness, or compatibility issues. It’s okay to feel disappointed, but remember not to let it define who you are or what you think of yourself.

Share some ways you use dating apps in real life. Being online can be impersonal, so when taking a photo on a dating app, say more than just “hi.” Browse their profile and see what interests you have in common to start a conversation, or start it with a compliment about their interests rather than just complimenting their physical attributes. Asking open-ended questions can also help build a connection. When taking a photo in person, you want to take the opportunity to make your presence known. Make eye contact and smile. Be aware of how you present yourself. You could even go so far as to tell the person how you came to record your show (e.g., I saw you come in and wanted to introduce myself). Keep it light, but remain confident in your presence and communication.

According to matchmaker Tennesha Wood of The Broom List and dating coach Monique Kelley, it doesn’t take a big gesture to get the ball rolling. Small, low-risk moves can be just as effective. Here are some easy ways to get started:

Ask a question: Approach in a casual, non-romantic way. Say something like, “You ordered the lamb—how is it? I’m thinking of trying it.” If he’s interested, he’ll continue the conversation and lead from there.
Pay a compliment: A simple comment like, “I love that shirt; that bold color looks great on you,” can open the door to more conversation. If he’s intrigued, he’ll engage and move things forward.
Use eye contact and smile: Sometimes a look and a smile can do more than words. If he is interested, he will try to continue contact.
Notification Details:Commenting on something specific, like his watch or the book he’s reading, can create a genuine interaction. A man who’s drawn in will prolong the moment.
Ask for a favor:Something as simple as “Could you hold my bag while I run to the bathroom?” or “Could you help me get something off the top shelf?” creates an opportunity to connect.
Be available: Smiling and striking up a conversation when you’re out is always a great way for women to get their picture taken. Flirting is an art form that has been sidelined by the rise of dating apps. However, many singles are suffering from dating app fatigue. So they’re going back to natural ways of meeting people. When you’re out, take a picture with the power of your smile and great conversation.
Make the most of the homecoming season: HBCU homecoming season is just around the corner! It’s the perfect time to try your hand at a college sweetheart (who’s single and divorced). Let her know you’ve always had a crush on her, even in college, and see where things go from there.
Lean on your friends: Let your friends know you’d like to date a single friend. Let them know that one of your friends has caught your eye. Keep in mind that some friends will say, “I don’t know about him, I’ve heard this and that… or my husband said this and that about him.” Just because he was in a relationship with one person doesn’t mean it will be the same for you. So tell them to reach out and you can decide to make a deal.
Practice: This is the best way to get your shot. Whether you’re at the gym, a running club, or the same yoga class, you can start building a relationship by letting them know you’re interested. Ask them to watch you lift weights, run with you during a running class, help you perfect your yoga pose, etc.

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