We have all been there. You’re at a friend’s house for a party or meet some friends out and BOOM — there she is. It’s like Michael Corleone getting hit by the “Thunderbolt” when seeing Apollonia for the first time in the Godfather.

The stars have aligned and in your good fortune she knows a friend of yours. You go over chat it up, make a good first impression, and get some important details about her (ie single). But now you approach that critical cross road of whether or not to pursue her.

She is a friend of a friend. Do you want to enter those potentially murky waters? On the one hand you have a shoe in, but on the other hand you can burn a whole friend group and ruin your reputation if things go south.

The Pros of Dating a Friend of a Friend

You have an easier in.

If you don’t get her number right away, you can always track it down later. This does not guarantee success but you should at least get an introduction.

Hopefully a good recommendation will go along with that introduction, otherwise F@#& that friend. Unlike approaching a woman in a bar or finding one on a dating app you’re not a total stranger, so the stranger danger meter is reduced which bodes well for your creepy ass.

Just like job hunting those with a recommendation have a leg up and an inherent advantage. So you should utilize your network because for both parties you are known commodities.

You can never underestimate the convenience factor.

Dating someone who runs in the same crowds reduces the anxiety or awkwardness of meeting new friends and making a good impression. There is also a much greater likelihood that your lifestyles will coincide.

If you smoke weed and you meet her through your weed friends then it’s probably an easier sell to get her to go to Burning Man. Having the same friend group limits the potential of those boring Saturday afternoons spent at your girlfriend’s random friend’s house where you don’t know anyone and have nothing in common with the guys.

You get reliable background checks.

If you meet Ms. Tits Hanging Out on Tinder (not always a bad thing) you don’t know if she is a battle-axe of a girlfriend who will wear you and your wallet out.

The benefit of a friend of a friend is that you can get some early intel. Is she chill, does she give head, and if she just got out of a relationship. This is helpful for obvious reasons because it gives you some hints on how to handle the relationship.

If she has a strong personality you know not to act like a macho man and make all the decisions of what to do and where to eat. If she has just exited a long relationship you know it’s likely she’ll want to take it slow with you. You don’t get this opportunity very often all this information should be used to your advantage.

Differentiating yourself from your competition.

Another pro in dating a friend of a friend is expanding your horizon by casting a larger net. If you are on dating apps looking for love there is the chance that you are coming across the same people on different platforms.

So by expanding your search to a girl in your network you are increasing your likelihood of finding a mate.

The Cons of Dating a Friend of a Friend

Unfortunately, there is a downside to every dating decision, including dating a friend of a friend.

The background check, as noted above, can also be detrimental.

If you have had some bad breakups or some publicized hookups, these can work against you. If you meet a woman at a bar or on an app most likely you are an anonymous Joe. However, if you have common connections your reputation may precede you and you may need to make a stronger case to prove your worth.

There are a lot of variables like how close the both of you are to the intermediary friend. If the intermediary is close to you, they will probably vouch for your character. If the woman who strikes your fancy is closer to the intermediary then they may be more protective. They may also be more protective if the woman is a co-worker because the intermediary doesn’t want to mess up their work environment with your garbage relationship antics.

You could lose your group of friends.

You never want to over-use your friends when it comes to having them set you up with their friends. Why? Well, if things go bad you could burn a friend group, or even if they don’t go bad a woman would have reservations in dating you if a couple of her friends have already gone down that lost highway.

You do not want to get the reputation of a player with your female acquaintances because they will never introduce you to one of their girlfriends. 

You’ll have to live with the consequences if things don’t work out.

Are you ready for the awkwardness of seeing this (friend of a friend) girl after you break up with her? Or even worse, are you willing to give up those friends if things end poorly?

Things could potentially get weird with other friends as well. Think about this scenario. In the beginning of your relationship with said girl, you send her a dick pic. Months later you break up. She’s part of your friend group now. What if she forwards the pic to all your friends? Yikes, unless of course you’re packing heat. At the end of the day, there will never be a clean break, so be prepared.

It’s easier to get caught up.

You may have to put your MegaDating strategy on hold. Talking and flirting with multiple girls at a time and going on several dates a week may be fine and easy to manage when none of them know you.

You can keep it secret and separate them all easily. But if your friends know what you are doing it may get back to your new Boo. She may not appreciate knowing that she is just another cog in your dating strategy because you are not giving her the individual attention that she thinks she deserves.

If you actually like her and think there is a future the best course of action would be honesty. If you are up front about MegaDating you can get ahead of any conflict.

You can tell her that you have been going on a lot of dates before meeting her but plan to take a break to see how things go with her. She should at least respect your honesty and hopefully see that you have serious intentions and are not just another F@#& Boy. 

How to Make Things Happen: Dating a Friend of a Friend

You have weighed your options and you want to move forward, but how do you do it? How do you cross that bridge from friend/acquaintance to dating/boyfriend? There are two roads to go down: you can be sly or you can be bold. 

The sly guy

The Sly guy may try to play it cool and figure out ways to keep “coincidentally” bumping into his target. Mr. Sly is looking to make things happen organically.

Maybe you keep on hitting up that intermediary friend to see what they are doing, or maybe you start hosting a few events or organizing nights out and keep inviting the intermediary in hopes that your true love will tag along.

You could also innocently follow her on Instagram to get an idea of her interests and if there are any events she is interested in. I would consider this light internet fact finding and not full on stalking, so I think you are in the clear.

The bold guy

The bolder move is to come out guns blazing; you know what you want so go get it. Don’t ask your friend for her number and don’t wait to send her a DM on Instagram.

You’re a big boy, be confident and get her number yourself. She will respect that and you’ll be starting off on a good foot. She won’t think, “wow I liked that guy but he didn’t even try to get my number.”

She doesn’t know you may be making moves behind the scenes to get that number, and even if you are it may be too late. The early bird gets the worm and strike while the iron is hot. You don’t know if she has a date tomorrow or if she’ll hit it off with someone else at the party. 

What if Things Don’t Work Out? 

If it turns out to be a huge mistake what do you do? Maybe you were a little inebriated, maybe you were a little lonely, or maybe your psycho radar was down for scheduled system maintenance.

You cannot ghost her but need to make an amicable exit because in this situation you have mutual acquaintances and there could be repercussions. A harmonious breakup is necessary to keep your good name intact, not burn any bridges, and to potentially have an ally and promoter of yours to future women.

A woman, in your friend circle, who you formally dated could be an asset, especially if you end on good terms. Things didn’t work out, it happens, but you’re both adults and can move on and be happy for each other. She is living breathing proof that you are a mature adult, and she can be the best advocate for you going forward.

It may not have worked out between the two of you but if you respect each other and like each other as human beings than you are in good shape. Now to have this cordial breakup you need to be honest and transparent.

When dating a friend of a friend, or anyone actually, you should set and agree upon expectations in the beginning. If you want to keep things light and leave options open; that is okay just discuss and both agree on it. If you want to then get serious then have that conversation.

If you both are not on the same page with moving to the next level, that may suck and it may be over but you should both be able to move on in a mature fashion. If you are getting to a point where you do not think there is a future, do not string her along, but cut that cord to free you both from a relationship that is not going to last.

Honesty and transparency are the keys to the exit because it leads to a level of trust and an ability to move forward without hard feelings which is the key to being able to co-exist as X’s within a friend group.

Dating a friend of a friend is not without risks but with proper planning and execution it can be entered into and potentially exited from without harmful consequences.

If you need further support with this topic, don’t hesitate to book a Zoom intro call with Emyli or a member of her team. 

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