The Gentleman’s Guide To Wedding Season

It’s that time of year again: Wedding Season! When a portion of your buds strap on the ol’ ball & chain and commit for eternity and making babies with their newly acquired companions.

It’s also the time of year that’s easy for you, the single 20-something or older, to drown yourself in fruit punch and wedding cake. You’re reminded constantly that you’re single and although you’re happy for your buddies, sometimes you’d rather just skip the reminder and forget about the reception all together. I want you to stop and realize one thing: Bridesmaids!

You know what I’m talking about. Bridesmaids get all dolled up for the occasion only to watch one of their best friends fulfill one of their lifelong dreams. So before you show up in your standard white shirt and tie, before you decide to show up 30 minutes late and leave immediately following your completion of the dreaded line, and before you pig out on meatballs and mini-sandwiches, consider this:

  • Approaching a single bridesmaid is as easy as it can get. Nothing softens up a girl and makes her more vulnerable than watching one of her best friends get married. She may be the bridesmaid, but in her mind she’s picturing herself wearing that white dress and is motivated beyond belief to find “the one”.

This is where you come in, you knight in shining armor you! Follow these simple tips and get ready to boom boom with the bridesmaids (figuratively of course)!


  1. Upgrade your wardrobe: Listen; bridesmaids dresses aren’t always the most flattering but that’s not the bridesmaid, that’s the bride making sure she’s the center of attention. You on the other hand have no excuse. Make a commitment and understand your needs, allot time and gather resources (a girl with fashion sense to help you out). How does a knight in shining armor ever get the girl without his shining armor?
  2. Get A Haircut: We know you may have spent all day at the lake, but your hair doesn’t need to suffer the same fate as your burnt skin. Like a first date, make sure you get your hair cut the week before and don’t try something new with it. And no, you don’t need to update to Beiber’s latest just to keep up with the Joneses.
  3. Hit The Gym: It’s not too late to get your swell on. Literally. Did you know that after lifting, your muscles begin to swell within 2 hours and can last for several days thereafter? What that means is that your muscles will actually appear larger and fill out your shirt better in case you’re not quite as toned as you would like to be. Note to any Ronnie Coleman wannabe’s out there: go easy on the juice, bro!
  4. Tan: Right about now you’re reading this thinking I just went all GTL on you. The Jersey Shore boys may have been on to something, although you don’t need a tanning bed to look good. Make sure your skin color is consistent and natural.
  5. Gather Intel: Talk with the bride and groom to be prior to the wedding day and let them know you’re interested in finding a girl. If they trust you, they will be eager to share with you any girls they deem as potential connections. The only exception may be the groom sharing his sisters or cousins (the future bride will be eager if she is close to them and knows/thinks you may be a match).
  1. Be A Gentleman: ALWAYS. This should go without saying.
  2. Confidence: This will single handedly make or break your impression. Confident, not cocky, just enough to make an impression stick.
  3. Make Sure She Is Single: This is super important prior to actively flirting. Just because she is there by herself doesn’t mean she is single. Still, make sure to introduce yourself and chat for a few moments. Use your judgement and conversation to determine if she’s single. If not, be charming but not flirtatious as she may have a cute single friend or sibling to introduce you to. 
  4. Flirt, Don’t Stalk: Make sure you find a way to introduce yourself and flirt with her throughout the reception, but don’t follow her around or interrupt her during important dialogue (use your own discretion). She’s stuck there supporting one of her best friends/family member, don’t make her feel more trapped than she already is. Peak her interest, walk away, find your way back or see if she does first.
  5. Work The Crowd: Don’t spend all your time in one place (typically around your other single friends); make sure you work your way around the room. You don’t know how well everyone is interconnected or what kind of allies you can make by striking up a short but simple conversation with someone you don’t know.
  6. Garter Toss – Look Interested: If a garter toss is part of the reception, you need to be there and look interested. This doesn’t mean you shove and push, but if it’s in your direction you need to put your hand up. All of the single women watch this and read into the level of interest you put into it. It shows that a) you’re single, and b) you’re showing interest in finding a companion.
  7. Dance: One of the most highly underrated things a single man can do at a wedding reception. Have fun and remember; a lot of women attribute the way you dance to the way… well… you know… flirt maybe? Show confidence and get others involved. Dancing with the cute little flower girl or get grandma in on the action. Know that if you’ve peaked your target’s interest at all earlier, she will notice you and think it’s “so cute.” Just make sure afterwards you approach her and ask her to dance.
  8. Sealing The Deal: Depending on how close you and your interest are with the couple getting married, sealing the deal can mean different things. If you have the opportunity, absolutely get her digits. If the reception is early enough, feel free to ask regarding her plans for that evening. Regardless of whether or not you got her digits, move onto the post-game.
  1. Call Her: If you got her digits and there is mutual interest, she is expecting you to call her and ask her on a date. Call her within 48 hours, there is no need to torture her any longer. The last thing you want to do is give up on you, or worse, forget about you entirely. Strike while the iron is hot, the whole wedding thing and mushy eternal companion thoughts are still heavy on her mind.
  2. Consult With The Bride: Cannot express this enough. If your interest is a bridesmaid or friend, what better reference is there than the bride in your corner? If you know the bride well, you’ve likely heard about her prior to the wedding and the bride has already told her all about you. Sometime after the couple gets back from the honeymoon, let the bride know your impression. If there is any mutual interest, the bride will be your biggest advocate. If you’re closer to the groom, play the angle and plan something with the couple after they get back from their honeymoon. If you made a big impression, the bride will already know the other side of the coin and will likely ask you if you met anyone at the reception. Admit it. If not, don’t worry, just make sure to raise the question and the bride may just tell you all about and advocate for her. The bride may even offer advice on how to connect the two of you.
  3. Build Off Of Your Prior Connection: When you do go out, make sure that your date plans are in line with and build off of whatever connection you made at the reception. Whether you immediately hit it off or heavily consulted with the bride for a reference and further introduction, build off of that.
  1. Remember Your Roots: You connected at a wedding/reception so keep that in mind as it will always be on hers as long as she is interested.
  2. Continue To Use Your Advocate: Involve the bride/groom as you had previously. Keep them in the loop. If your girl is a bridesmaid, she will remain close to the bride especially in the early going as the bride transitions into married life. They are the happy honeymooners, and if they are close to your girl, they will be more than happy to support you as your girl decides whether or not to transition her wedding goggled crush into a full fledged relationship and beyond.
  3. If Necessary – Let Her Down Gently: Don’t make your mutual friends look like fools. Make sure she is the first to know, and soon after share the news briefly with your advocates. Let them know that you are no longer seeing her, but don’t go into private details as they will make it full circle. 
BUT – What if you don’t have the bride/groom’s full support?
  1. Work Fast: Whether they think you’re a player or just know your tendencies all to well, you’re going to have to move very fast if you hope to seal the deal on anything with her. If she’s close to either the bride or groom, they’ve likely issued some kind of warning.  Whatever your intention with her; you better make a big impression and strike fast before any of her other friends issue an even bigger warning. By working fast, you can overcome her objections and enact your master plan with as minimal resistance as possible. Failure to act quickly and you’ll be left with a swift slap in the face (hopefully not literally) as she ignores your calls/texts and any future advances.
  2. Find Out Her Intentions: She may have received a warning about you, but that may not stop her. It’s no secret that girls like bad boys and guys with an edge, so it shouldn’t come as a surprise that she will be willing to feel you out for herself. Find out her intentions and choose your angle; whether you take them head on or need to play it out more.


  1. Have A Clue What You Want: If all you want is a fling, make sure to take the risks necessary and understand the impression it will leave if you are successful. 
  2. Have Fun: The biggest law of attraction at a wedding/reception is to have a good time and express confidence. Nobody wants a downer, especially at such a happy event as a wedding.
  3. Support The Bride & Groom: Always talk about them in good favor and share good memories that are relevant. Nobody wants to hear the story of how many girls your buddy played or dated before he met the bride. It will discredit your buddy, discredit you, and might get you called out and punched in the face by the groom or any of his/your friends or family.
  4. Sneak In Something For Yourself: Granted, a wedding/reception is not all about you, but make sure you take time to get away from the comfort of the people you already know and mingle with the single ladies and sneak in some action.

There you go, gentleman! Now that you have the outline, go out there and make it happen. You can even do it in pairs. Any questions?

No? OK, time to go boom boom with the bridesmaids!

This entry was posted in Dating, Single Life, Uncategorized. Bookmark the permalink.

One Response to The Gentleman’s Guide To Wedding Season

  1. What does Boom Boom mean? haha

    Very detailed blog post! I actually thought the tips were pretty good! You have to print these out and post them in singles wards around the country. 😉 It sounds like you have a LOT of experience with this. Which leads me to think one thing: you are a serial dater.

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