Being in prison doesn’t stop people from desiring fulfilling dating lives and a genuine human connection. An incarcerated person named Jeremy Meeks found a new love and a new career as a professional model after his release from prison. A prison sentence isn’t the end of a person’s story, but sometimes they need help finding that next chapter in their life.

Whether you’re currently incarcerated or interested in connecting with a prisoner, certain niche sites and apps can help establish a pen pal relationship that could lead to more. It’s free to create a profile, so a single person can unlock romantic possibilities without needing a credit card.

Overall Best Prison Dating Sites for Pen Pals

Prison dating sites can typically be accessed in prison libraries, and some popular dating sites have proven useful for all types of singles as well. Here is our ranking of the overall best dating sites for prisoners and their admirers.

Category Rating
★★★★★ 4.9/5.0
  • Match is the world’s longest running dating site
  • The Discover section has search filters by interests, looks, lifestyle, and more
  • Match is available in 50 countries and 15 languages

Match is a unique dating website that prioritizes real connections and love stories. The platform is perfect for hopeless romantics seeking a relationship based on common values. 

Match takes the stress out of matchmaking by providing plenty of guidance and support along the way. When users create a free account, they input personal information date preferences to inform the match algorithm. The matchmaking system curates a shortlist of desirable matches based on the profile information provided. So be sure to be honest about your interests and situation to increase the likelihood of a good match.

The Match algorithm gives you the best possible matches who meet your requirements and preferences, and it is welcoming to any single adult user who is over 18.

2. Meet-An-Inmate

Prison can isolate individuals from meaningful connections and foster negative emotions of hopelessness and despair. But it doesn’t have to be that way. Meet-An-Inmate aims to bring a pocket of joy to prison life. 

Prison inmate in orange jumpsuit with hand tattoos holding smartphone through cell bars
Prison may feel isolating, but there are plenty of websites for prison dating.

Since 1998, Meet-An-Inmate has brought people together and introduced single inmates to a wider world of human relationships. Members start by selecting their gender (male or female options online), and they can choose the gender of the inmate they wish to communicate with via letter writing. This system isn’t overtly for romance, but many people, both free and incarcerated, use it that way.

Meet-An-Inmate offers a heartfelt way for prisoners and their pen pals to get to know one another one letter at a time. People can be themselves and dive into each other’s passions and dreams. The Meet-An-Inmate team encourages people to create a space of respect, dignity, and compassion in these epistolary conversations.

3. WriteAPrisoner.com

A good pen pal is more than just a writing buddy. Their letters or messages can help keep inmates grounded and remind them of the beauty in life. WriteAPrisoner is a web service where users can find a confidant and friend while serving a prison sentence. 

Having a pen pal on the outside can be comforting for single prisoners because the written communication can provide a source of inspiration, care, and even love. WriteAPrisioner provides an avenue for single people to be vulnerable and create a deep connection with prisoners.

Best Prison Dating Sites for Senior Singles

Prisoner Dating is more common than most people know, and it’s not just a young person’s game. Older singles who have been in prison for years may seek companionship and conversation from people online. Here’s a list of some safe platforms that work for prison pen pals in their senior years.

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★★★★★ 4.5/5.0

Silver Singles reminds people that age is just a number, and love is always possible. Silver Singles creates a safe space for more seasoned singles to find a partner in the same age range.  

The signup process includes a compatibility quiz that highlights personality traits and date preferences. Silver Singles members can disclose important lifestyle information in their profile bio. Silver Singles prioritizes quality over quantity in its matchmaking. The majority of singles in this user base are over 50 and looking for a real connection, so it’s a good opportunity for a single prisoner hoping to start fresh in a new relationship.

Category Rating
★★★★★ 4.9/5.0
  • Thousands of success stories from all over the world
  • Find senior dates using advanced search filters and match suggestions
  • The Help Center offers quick tips and guidance

As part of the Match Group family, the dating app OurTime offers valuable dating tools to save time and spark senior relationships. OurTime supports a unique online dating experience where older singles have control over their love lives and needn’t bother with younger matches. 

OurTime removes any stigma against advanced age and gives single people, including prisoners, the chance to meet people with similar backgrounds and interests. After new users create a free account, they can browse local prospects and send messages to the most compatible matches. Top Picks can chat for free in OurTime. If they’re looking for additional features, OurTime users have the option to upgrade to a premium subscription with a two-week trial period.

6. Inmate Passions

Inmate Passions is a niche dating site for singles who want to engage in prisoner dating. The dating site is run by the Passions Network and has a lot of communication and community features available. It’s free to join Inmate Passions and browse matches with similar interests and backgrounds.

Screenshot of InmatePassions website
InmatePassions can help prisoners connect with the outside world.

The online dating site description discusses its core values of love and acceptance, urging single people to keep an open mind as they explore a new relationship.  This niche site has dedicated tools for incarcerated members and their potential matches outside of prison. It’s an opportunity for singles to meet without judgment and explore connections with honesty and respect. 

7. LoveAPrisoner.com

A single prisoner faces challenges in the dating world because they need a partner to look past their current imprisonment and criminal history. That’s a tall order, but it’s not impossible on a prisoner dating site like LoveAPrisoner

LoveAPrisoner website screenshot
LoveAPrisoner offers people the chance to connect beyond the bars of a cell.

LoveAPrisoner aims to connect incarcerated people, former convicts, and other free persons in a dating network where the past needn’t define the present.

LoveAPrisoner introduces its members to a pen pal. Its matchmaking gives prisoners something to look forward to after their sentence is served. New users can scroll through a list of prisoners and select those they wish to talk to based on the profile’s photo and biography information.

Best Prison Dating Sites for Naughty Escapades

Single adults have needs, and incarcerated people often feel an especially strong urge to find intimacy and release their pent-up sexual energy. Hookup sites can be a good avenue for exploring sexual encounters without needing to leave a prison cell or go too far outside your comfort zone. Check out the following free sites for casual hookups and sexting.

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★★★★★ 4.7/5.0

Adult Friend Finder is a popular hookup site that serves online daters looking for a good time with no strings and few judgments. Everyone on this adult dating website is interested in sexual exploration, both online and offline, so it isn’t hard to attract a sexting partner. 

The AFF website accommodates all tastes, kinks, fetishes, and lifestyles. The registration process is free and straightforward so lonely prisoners can skip the paperwork and get straight to flirting and matchmaking.  Users can opt for premium membership if they want to send unlimited messages and remove ads. The paid membership isn’t necessary for prisoners seeking erotic content and an online fling. Plenty of the forums and photo galleries are accessible with a free account.

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★★★★★ 4.8/5.0
  • A global network of naughty singles over 18
  • Ability to blur nude and explicit content, if desired
  • Advanced search filters and one-on-one messaging

BeNaughty can help single people be honest about their desires and establish a flirtatious relationship without the need for tedious small talk. Just as the name implies, BeNaughty has become a hub for daters focused on getting freaky and acting a little naughty online. 

The signup process keeps personal information to a minimum, so prisoners can be a little naughty and hold back photos or life details in their profile.  BeNaughty has instant messaging and video chat features available to start romantic connections on the web. This user-friendly interface can support inmates who want to connect with sexy adults and let go of their inhibitions, at least for a little while.   

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★★★★★ 4.5/5.0

The hookup site known as OneNightFriend gets straight to the point with its sexy profile setup and fast matchmaking tools. The website uses a location-based match system, so finding local dates for a one-night stand or conjugal visit isn’t too complicated.

Once OneNightFriend users create a dating profile (no photos required), they can use the like system to get the attention of potential date prospects and spark new chats. Free members have limited communication ability, but they can respond to messages from premium members. OneNightFriend also offers complimentary prewritten messages to break the ice with a local hottie.

Category Rating
★★★★★ 4.5/5.0
  • A massive user base of over 70 million dating profiles
  • Send a free private message or Flirtcast to get something going
  • Exchange nude pics or adult videos with a Flirt member you trust

Sometimes it pays to be a flirt. Flirt.com is the website that makes being a tease a good thing. Flirt.com users can create their own steamy chat and explore potential matches with no strings attached. The hookup site can even support communication with a prison pen pal.

Single prisoners do not have to worry about how to start a new conversation. Flirt has a chat feature called Flirtcast that sends a prewritten greeting to multiple users at once. This helps single people increase the possibility of getting interactions with a new match. It could save a lot of time in the online dating scene, and it takes the pressure off singles to come up with an icebreaker on their own.

Love Has No Bars Thanks to Online Dating

True love can overcome physical distance by going online, and singles should take advantage of modern technology to meet new people in all sorts of circumstances. A single person in prison needn’t stop having a personal life – prison dating sites can help keep conversations going and feelings growing. 

Using online websites to connect with prisoners could be the start of a new friendship or romance. A free person can completely change a prisoner’s life and conditions in incarceration simply by saying hello and offering their time as a friendly pen pal. All it takes is one right match to set the heart free and open the door to new opportunities for friends beyond the wall.

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