Single With Siggy: The 'Stand-In Boyfriend'

ERICA, 31: For the past five years, I've been with this same guy, but he won't commit—I call it a "situationship," not even a "relationship." When we hang out, we mostly stay in and order takeout, but we talk almost every day. I've tried to walk away, but I always compare other guys with him.

SIGGY: Sure, because you're still attached! It's like wearing Uggs. You know you have to wear heels, but really you just want to curl up on your couch and wear slippers. You've made it too comfortable for him. Is he your age?

ERICA: Yes.

SIGGY: I want you to date someone older. When you were in college, it made sense to date guys your age; that's who you met. Now you need a mature and compassionate man.

ERICA: Should I stop taking his calls?

SIGGY: No. Say, "Hi, how are you? I'd love to talk, but I'm about to go out on a date."

ERICA: Actually, every time I went on a date, he'd call. It's like he had a radar.

SIGGY: Act as if nothing bothers you. Like, "You want to put me in the friend zone? Watch what type of friend I can be." Men love a challenge.

ERICA: I'm not a challenge. I'll say, "We can't talk anymore."

SIGGY: No, that means you care. Meet him for lunch. "Oh, hi, work is great, I'm dating." You'll either drive him crazy and get him over the hump, or you'll date older, wiser men and they'll turn you off him. You win either way.

ERICA: He'll call at 12:30 on Saturday night. What am I going to do, not answer the phone?

SIGGY: Don't ever answer the phone on Friday or Saturday! Those are for dates. It's none of his business what you're doing on Saturday at 12:30 a.m. My whole point here is to drive him insane.

Two weeks later, after following Siggy's advice …

ERICA: I've gone out on a few dates—my first one with an older man is next weekend. As for my ex, it was uncomfortable to have quick little conversations. He doesn't like that I'm dating.

SIGGY: He has to man up and do something about it! By dating, you're saying, "I'm worthy of a relationship." And dating men who are 35 to 39—that's in your age group. It's not old.

ERICA: It's like I'm coming out of my comfort zone. Before, I thought, I'll be ready to date when I'm over him. But going out took my mind off of it.

SIGGY: People say, "Oh, I have to lose 10 pounds" or "I have to finalize my divorce." You can't put it all on hold.

ERICA: Right. If I really waited, I'd never go out with anyone!

SIGGY: The more you do it and fall flat on your face, the more you'll be OK. "It didn't hurt that bad! It was OK!" That's what life is about.