200 Fun, Flirty, & Deep Questions to Get to Know a Guy Better
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QuestionWhat's the most important thing when it comes to making a relationship with a big age gap work?
Erika KaplanErika Kaplan is a Dating Coach and Matchmaker for Three Day Rule, an exclusive matchmaking company across fifteen cities in the United States. With over eleven years of experience, Erika specializes in helping singles find quality matches through date coaching and premium matchmaking services. Erika graduated from Penn State with a Bachelor’s degree in Public Relations. She worked for Rolling Stone, Us Weekly, and Men’s Journal before leaving publishing to pursue her passion for connecting people. Erika has been featured on Lifetime, the Philadelphia Inquirer, and CBS as well as in Thrillist, Elite Daily, Men’s Health, Fast Company, and Refinery29.
MatchmakerFinding your shared values is absolutely essential. The things you have in common are key, and bonding over those core beliefs is really important when it comes to the longevity of a relationship. -
QuestionHow can I attract a guy who is a little older than me?Erika KaplanErika Kaplan is a Dating Coach and Matchmaker for Three Day Rule, an exclusive matchmaking company across fifteen cities in the United States. With over eleven years of experience, Erika specializes in helping singles find quality matches through date coaching and premium matchmaking services. Erika graduated from Penn State with a Bachelor’s degree in Public Relations. She worked for Rolling Stone, Us Weekly, and Men’s Journal before leaving publishing to pursue her passion for connecting people. Erika has been featured on Lifetime, the Philadelphia Inquirer, and CBS as well as in Thrillist, Elite Daily, Men’s Health, Fast Company, and Refinery29.
MatchmakerLean into your more mature and independent side. Showing people that you're confident and comfortable in your skin is really a big component of this. Also, you have to position yourself in social circles so that you're around people slightly older than you. -
QuestionIs it possible for a 68-year-old woman to have a successful relationship with a 26-year-old man?
RakshiahCommunity AnswerGenerally, it is very challenging for a 68-year-old woman and a 26-year-old man to have a successful relationship. The significant age gap often means you are at very different life stages, with divergent priorities, energy levels, and social experiences. These differences can make maintaining a healthy, balanced relationship extremely difficult. -
QuestionI am 13 years old and interested in a 10-year-old. Is this an acceptable age difference?
RakshiahCommunity AnswerFor individuals who are 13 and 10 years old, this age difference is generally considered normal and acceptable. It is important to ensure mutual respect, comfort, and to keep interactions age-appropriate.
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QuestionI am 37 and my girlfriend is 20. We have been dating for a month, and I am wondering if this age difference is generally considered acceptable.
RakshiahCommunity AnswerDating with a 17-year age difference can work, but it really depends on your individual maturity and compatibility. Since you've only been dating for a month, it's wise to take things slow, communicate openly, and ensure you're both aligned on your goals and feelings. While age is just a number, mutual respect and understanding are crucial for a successful relationship.
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QuestionI am 16 years old and have reciprocated feelings for a 13-year-old girl who confessed her love for me. Is this age difference acceptable, or should I reconsider pursuing a relationship?
RakshiahCommunity AnswerIf you and the other person both have feelings for each other, and you are comfortable with the relationship, a three-year age gap is often not considered a major difference and is quite common. It is a personal decision if both individuals are happy and ready for the relationship.
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QuestionI am 24 and my partner is 20. Is this a concerning age gap, especially since he has only recently left his teenage years?
RakshiahCommunity AnswerA four-year age gap is generally not considered significant. You also recently transitioned out of your teenage years, so a substantial contrast in life experience may not be present.
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