I'd really like to tell my DF in a cute way this time around (DS was an "oopsie" baby, so he was right there waiting for the result with me, lol). I'm not really sure how I'm going to do it though, with him or my family members.
I was thinking about giving him a poppy seed bagel for breakfast and then cooking a dinner with all "baby" related food items (baby carrots, baby corn, lamb, ect) and see if he takes the hint.
Our anniversary is also in June, so if we get pregnant right away (we might be trying in May) then I could always buy or make a cake with a special message on it to let him know that we're pregnant or for Father's Day I could give him a card that is from both DS and baby #2 and tape the positive test inside. If we don't get pregnant right away though then I'm not really sure exactly how I'll tell him barring the food idea.
As far as family goes I was thinking that we could maybe pick up a children's book of some kind and give a copy to each set of parents with a note on the inside that says something along the lines of "Please read this to us sometime! From DS and his little brother or sister"
If you're planning to try in late summer then you could always tell people with your Halloween costume if you get pregnant before then. If you get pregnant right away you should be around 12 weeks by then. A lot of women have done pregnancy related costumes (like dressing up as an oven and taping a picture of a bun to their tummy) as their way of telling people that they're pregnant.