Been out of the dating game for a while
However, Oshima also recommends keeping your options open—give him competition.That guy may never open up to the idea of a relationship, and you don’t want to end up heartbroken.When you ask, make sure it’s face to face, because nothing beats real-life interaction.*Sidenote, I also want to say that I’m a firm believer that whoever does the asking should also do the paying. My wife Deb has some articles out there about the women doing the asking, but that’s a topic for another day.So you’ve just gone on your first date, and you took initiative, now it’s time to be direct.Before we dig in to this topic, let me introduce myself.First and foremost, I’m a guy…so I’d like to specifically address the men out there today.” It always helps if you actually give a time-frame, rather than leaving it open ended.This way it’s harder for them to say no, but it also makes it a lot more clear when things are going to happen.
Threatening him with an ultimatum isn’t a good idea; give him time to see how wonderful you are!You’ve been seeing this dude for three months, and every time you bring up the completely un-crazy notion of a relationship, he totally shuts down.“If every time you bring up the 'girlfriend' concept he shuts down, the worst thing you can do is to put more pressure on him,” Oshima says.After all, you want a man who romantic; he held your hand and gave you a kiss.
But the next day, he seemed kind of weird and distant. “It sounds like he's probably unsure of his feelings, or the feelings he experienced the night before may be something so new to him that it may be making him feel a little scared,” says Suzanne Oshima, a matchmaker and dating coach at Single in Stilettos.
That could even be the next day (I do think texting them on the drive home is a: unsafe, and b: a Now for the slice of awkward cake: if things did NOT go well…should communicate that you are glad you got the chance to hang out but you think it would be better if we were friends. While it will be awkward the next time you see that person (I don’t think there’s anyway around that), at least you were open and honest, so that both of you can move on.