[AskApril Masini]

First of all, if a woman likes you she’ll look at you and hold you gaze. You may catch her looking at you when she thinks you’re not going to see her doing it. She’ll play with her hair and primp to look attractive to you. Those are all signs that she’s attracted to you.

But even with those signs a lot of men are worried about getting their feelings hurt by rejection, and I’m sorry, but there’s no good short cut! It’s really important for you to get up to bat and see if you can hit a home run or even a grand slam. If you never try, you’ll never know, and since you’re 38, it’s time to give it a go.

Look, worst thing that happens is she’s not interested in you as anything more than a friend. And if that’s the case, then at least you know where you stand with her. Best case is that she’s been waiting for you to make a move. My advice to you is to amp this relationship up to the next level and see what’s there between the two of you.

Ask her to go out on a Saturday night, but ask her in advance, as if it’s a real date. And if you usually go to the movies and the coffee shop afterwards, plan this outing so that there’s no mistaking it for anything but a date. Take a risk with this woman. Like I said, worst case is she just wants to be friends, but best case is she’s wildly pleased and has been waiting for you to show up as prince charming and not just the guy who’s her best friend.